HCID 69707938, compound → [1-(4-hydroxy-butyl)-2-(3-vinyl-indazol-1-ylmethyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester

HRID 896368Notes

Reaction equation

HRID 896368 reaction equation
C(OC(=O)NCC1C=CC2N(CCCCO)C(CN3C4C(=CC=CC=4)C(=O)N(C4CC4)C3=O)=NC=2C=1)(C)(C)C.[C:40]([O:44][C:45]([NH:47][CH2:48][C:49]1[CH:80]=[CH:79][C:52]2[N:53]([CH2:68][CH2:69][CH2:70][CH2:71][O:72]C(=O)C(C)(C)C)[C:54]([CH2:56][N:57]3[C:65]4[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=4)[C:59]([CH:66]=[CH2:67])=[N:58]3)=[N:55][C:51]=2[CH:50]=1)=[O:46])([CH3:43])([CH3:42])[CH3:41]>>[C:40]([O:44][C:45](=[O:46])[NH:47][CH2:48][C:49]1[CH:80]=[CH:79][C:52]2[N:53]([CH2:68][CH2:69][CH2:70][CH2:71][OH:72])[C:54]([CH2:56][N:57]3[C:65]4[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=4)[C:59]([CH:66]=[CH2:67])=[N:58]3)=[N:55][C:51]=2[CH:50]=1)([CH3:41])([CH3:42])[CH3:43]

Participants

3

Reactant 2

HCID 69707938HCID 69707938, compoundHCID 69718999[2-(3-Cyclopropyl-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-ylmethyl)-1-(4-hydroxy-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester

Product 1

HCID 69719540[1-(4-hydroxy-butyl)-2-(3-vinyl-indazol-1-ylmethyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl esterYield 74.5%

Procedure

The procedure for the preparation of [2-(3-cyclopropyl-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-ylmethyl)-1-(4-hydroxy-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester was followed (reaction time 3 hrs.) starting from 2,2-dimethyl-propionic acid 4-[5-(tert-butoxycarbonylamino-methyl)-2-(3-vinyl-indazol-1-ylmethyl)-benzoimidazol-1-yl]-butyl ester (215 mg, 0.384 mmol). Purification by flash chromatography (eluent 3%, 4% methanol in DCM) afforded [1-(4-hydroxy-butyl)-2-(3-vinyl-indazol-1-ylmethyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester (136 mg, 74%) as a white foam:

Workup

  1. custom(reaction time 3 hrs.)
  2. customPurification by flash chromatography (eluent 3%, 4% methanol in DCM)

Sources & evidence

ORD record
ord-39ff9bea1326436680e86bf010cc8cf1
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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