Ammonium Hydroxide → HCID 178486473, compound

HRID 1014471Notes

Reaction equation

HRID 1014471 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]2[N:17]=[C:16]([NH:18][C:19]3[CH:27]=[C:26]4[C:22]([CH2:23][CH2:24][NH:25]4)=[CH:21][C:20]=3[O:28][CH3:29])[NH:15][C:14]3=[N:30][CH:31]=[CH:32][C:13]=23)[C:3]=1[C:4]([NH2:6])=[O:5].Br[CH2:34][C:35](Cl)=[O:36].[NH4+:38].[OH-]>C1COCC1>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]2[N:17]=[C:16]([NH:18][C:19]3[CH:27]=[C:26]4[C:22]([CH2:23][CH2:24][N:25]4[C:35](=[O:36])[CH2:34][NH2:38])=[CH:21][C:20]=3[O:28][CH3:29])[NH:15][C:14]3=[N:30][CH:31]=[CH:32][C:13]=23)[C:3]=1[C:4]([NH2:6])=[O:5]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 89602Bromoacetyl chlorideHCID 178486468HCID 178486468, compound

Product 1

HCID 178486473HCID 178486473, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A −40° C. solution of 2-fluoro-6-[(2-{[5-(methyloxy)-2,3-dihydro-1H-indol-6-yl]amino}-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]benzamide (70 mg, 0.16 mmol) in THF (20 mL) was treated with a solution of bromoacetyl chloride (25 mg, 0.16 mmol) in THF (1 mL). After 5 min a 27% aqueous NH4OH solution was added and the reaction mixture was stirred at rt overnight. The resulting slurry was filtered and the solid washed with Et2O to obtain 2-fluoro-6-[(2-{[1-glycyl-5-(methyloxy)-2,3-dihydro-1H-indol-6-yl]amino}-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]benzamide as a grey solid (67 mg, 86%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.07-3.19 (m, 2H), 3.44, (s, 2H), 3.78 (s, 3H), 3.97-4.10 (m, 2H), 6.23, (s, 1H), 6.82-7.04 (m, 3H), 7.27-7.41 (m, 1H), 7.60 (s, 1H), 8.02 (s, 1H), 8.10 (s, 1H), 8.51 (d, J=7.61 Hz, 1H), 8.67 (s, 1H), 10.53 (s, 1H), 11.33 (s, 1H) a CH2 signal with 2 protons is missing, may overlap with water peak in sample; ESIMS (M+H)+=491.26.

Workup

  1. filtrationThe resulting slurry was filtered
  2. washthe solid washed with Et2O

Sources & evidence

ORD record
ord-035ba809c49c4e9eab2efda82161b366
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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