Diisopropylethylamine → HCID 67355233, compound

HRID 1850597Notes

Reaction equation

HRID 1850597 reaction equation
[CH:1]1([N:7]2[C:11]3[N:12]=[C:13]([NH:16][C:17]4[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][N:18]=4)[N:14]=[CH:15][C:10]=3[CH:9]=[C:8]2[C:26](=[O:30])[N:27]([CH3:29])[CH3:28])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:64]([O:68][C:69]([N:71]1[CH:76]2[CH2:77][CH2:78][CH:72]1[CH2:73][NH:74][CH2:75]2)=[O:70])([CH3:67])([CH3:66])[CH3:65]>CN(C=O)C>[C:64]([O:68][C:69]([N:71]1[CH:72]2[CH2:78][CH2:77][CH:76]1[CH2:75][N:74]([C:21]([C:20]1[CH:19]=[N:18][C:17]([NH:16][C:13]3[N:14]=[CH:15][C:10]4[CH:9]=[C:8]([C:26](=[O:30])[N:27]([CH3:29])[CH3:28])[N:7]([CH:1]5[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]5)[C:11]=4[N:12]=3)=[CH:25][CH:24]=1)=[O:22])[CH2:73]2)=[O:70])([CH3:67])([CH3:65])[CH3:66]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 157409088-Boc-3,8-diaza-bicyclo(3.2.1)octaneHCID 67354845HCID 67354845, compound

Product 1

HCID 67355233HCID 67355233, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 1 mL DMF solution of 6-(7-cyclohexyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-nicotinic acid (50 mg, 0.122 mmol) was added DIPEA (32 mg, 0.043 mmol) and HBTU (49 mg, 0.129 mmol). After stirring for 15 m at room temperature 3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (31.2 mg, 0.147 mmol) was added and the reaction mixture was left to stir at room temperature for 4 h. The reaction was quenched by pouring into brine and extracted with EtOAc. The organic extracts were dried with Na2SO4, filtered and concentrated. The crude product was purified by NP-LC (Analogix, 10% MeOH in EtOAc) to yield 3-[6-(7-cyclohexyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridine-3-carbonyl]-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (60 mg, 0.10 mmol). MS m/z 603.5 (M+H)+.

Workup

  1. additionwas added
  2. waitthe reaction mixture was left
  3. customThe reaction was quenched
  4. additionby pouring into brine
  5. extractionextracted with EtOAc
  6. dry with materialThe organic extracts were dried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by NP-LC (Analogix, 10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-39ba6745883846f5b727607d63671b9f
Source dataset
uspto-grants-2015_02
Patent number
US08957074B2

Reaction notes

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