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Hydrochloric Acid → HCID 69707938, compound

HRID 896367
Notes
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Reaction equation

HRID 896367 reaction equation
C(OC(=O)NCC1C=CC2N(CCC(C)C)C(CN3C4C(=CC=CC=4)C(=O)N(C4CC4)C3=O)=NC=2C=1)(C)(C)C.[CH:40]([C:42]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[NH:44][N:43]=1)=[CH2:41].[C:51]([O:55][C:56]([NH:58][CH2:59][C:60]1[CH:81]=[CH:80][C:63]2[N:64]([CH2:69][CH2:70][CH2:71][CH2:72][O:73][C:74](=[O:79])[C:75]([CH3:78])([CH3:77])[CH3:76])[C:65]([CH2:67]Cl)=[N:66][C:62]=2[CH:61]=1)=[O:57])([CH3:54])([CH3:53])[CH3:52].Cl>>[C:51]([O:55][C:56]([NH:58][CH2:59][C:60]1[CH:81]=[CH:80][C:63]2[N:64]([CH2:69][CH2:70][CH2:71][CH2:72][O:73][C:74](=[O:79])[C:75]([CH3:78])([CH3:77])[CH3:76])[C:65]([CH2:67][N:44]3[C:45]4[C:50](=[CH:49][CH:48]=[CH:47][CH:46]=4)[C:42]([CH:40]=[CH2:41])=[N:43]3)=[N:66][C:62]=2[CH:61]=1)=[O:57])([CH3:54])([CH3:52])[CH3:53]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 11051787HCID 11051787, compoundHCID 59561852HCID 59561852, compoundHCID 69718855[2-(3-cyclopropyl-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester

Product 1

HCID 69707938HCID 69707938, compound
Yield 71%

Procedure

The procedure for the preparation of [2-(3-cyclopropyl-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester was followed starting with 3-vinyl-1H-indazole (140 mg, 0.970 mmol) and 2,2-dimethyl-propionic acid 4-[5-(tert-butoxycarbonylamino-methyl)-2-chloromethyl-benzoimidazol-1-yl]-butyl ester; HCl salt (474 mg, 0.614 mmol). After quenching with water, a gum formed. The water was decanted and the residue partitioned between diethyl ether and water. The layers were separated and the aqueous phase extracted with diethyl ether (2×40 mL). The combined organic phases were washed with water (twice), brine, and dried (MgSO4). Purification by flash chromatography (eluent hexane-acetone 2:3) afforded 2,2-dimethyl-propionic acid 4-[5-(tert-butoxycarbonylamino-methyl)-2-(3-vinyl-indazol-1-ylmethyl)-benzoimidazol-1-yl]-butyl ester (386 mg, 71%) as a colorless foam:

Workup

  1. customAfter quenching with water
  2. customa gum formed
  3. customThe water was decanted
  4. customthe residue partitioned between diethyl ether and water
  5. customThe layers were separated
  6. extractionthe aqueous phase extracted with diethyl ether (2×40 mL)
  7. washThe combined organic phases were washed with water (twice), brine
  8. dry with materialdried (MgSO4)
  9. customPurification by flash chromatography (eluent hexane-acetone 2:3)

Sources & evidence

ORD record
ord-1aa069294f4642f6ad6b66b101511d63
Source dataset
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06919331B2

Reaction notes

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