N,O-Dimethylhydroxylamine → HCID 178486477, compound

HRID 1014473Notes

Reaction equation

HRID 1014473 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][N:25]4[C:28](=[O:32])[CH2:29][NH:30][CH3:31])=[CH:21][C:20]=3[O:33][CH3:34])[NH:15][C:14]3=[N:35][CH:36]=[CH:37][C:13]=23)[C:3]=1[C:4]([NH2:6])=[O:5].CN[O:40][CH3:41]>>[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:28](=[O:32])[CH2:29][N:30]([CH3:31])[O:40][CH3:41])=[CH:21][C:20]=3[O:33][CH3:34])[NH:15][C:14]3=[N:35][CH:36]=[CH:37][C:13]=23)[C:3]=1[C:4]([NH2:6])=[O:5]

Participants

3

Reactant 2

HCID 14232N,O-DimethylhydroxylamineHCID 178484661HCID 178484661, compound

Product 1

HCID 178486477HCID 178486477, compound

Procedure

One third of the reaction mixture from the preparation of 2-fluoro-6-[(2-{[1-(N-methylglycyl)-5-(methyloxy)-2,3-dihydro-1H-indol-6-yl]amino}-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]benzamide was treated with N,O-dimethylhydroxylamine (145 mg, 2.37 mmol) and KI (90 mg, 0.54 mmol). After 1 h the resulting mixture was concentrated onto Celite and purified by silica gel chromatography using 1-10% MeOH (containing 0.2% NH3)/CH2Cl2 to obtain 2-fluoro-6-[(2-{[1-[N-methyl-N-(methyloxy)glycyl]-5-(methyloxy)-2,3-dihydro-1H-indol-6-yl]amino}-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]benzamide as a yellow solid (43 mg 42%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.59 (s, 3H), 3.08-3.20 (m, 2H), 3.43 (s, 3H), 3.60 (s, 2H), 3.78 (s, 3H), 4.22 (t, J=8.26 Hz, 2H), 6.23 (s, 1H), 6.81-6.92 (m, 1H), 6.95 (s, 1H), 6.97 (s, 1H), 7.28-7.40 (m, 1H), 7.61 (s, 1H), 8.02 (s, 1H), 8.10 (s, 1H), 8.51 (d, J=8.42 Hz, 1H), 8.63 (s, 1H), 10.54 (s, 1H), 11.31 (s, 1H); ESIMS (M+H)+=535.18.

Workup

  1. concentrationAfter 1 h the resulting mixture was concentrated onto Celite
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-b0cd01d134ed4b728db5cd6001a5ab64
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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