HCID 59441997, compound → HCID 178486656, compound

HRID 1014512Notes

Reaction equation

HRID 1014512 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:21][C:22]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:23]=2[C:24]([NH2:26])=[O:25])[C:5]2[CH:10]=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:6]=2[N:7]=1.[NH2:32][C:33]1[CH:41]=[C:40]2[C:36]([CH2:37][CH2:38][N:39]2[CH2:42][C:43]([N:45]([CH3:47])[CH3:46])=[O:44])=[CH:35][C:34]=1[O:48][CH3:49]>>[CH3:47][N:45]([CH3:46])[C:43](=[O:44])[CH2:42][N:39]1[C:40]2[C:36](=[CH:35][C:34]([O:48][CH3:49])=[C:33]([NH:32][C:2]3[NH:7][C:6]4=[N:8][CH:9]=[CH:10][C:5]4=[C:4]([NH:21][C:22]4[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:23]=4[C:24]([NH2:26])=[O:25])[N:3]=3)[CH:41]=2)[CH:37]=[CH:38]1

Participants

3

Reactant 2

HCID 59441997HCID 59441997, compoundHCID 866441882-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzamide

Product 1

HCID 178486656HCID 178486656, compoundYield 6%

Procedure

In a manner analogous to General Protocol III, 2-[(2-{[1-[2-(dimethylamino)-2-oxethyl]-5-(methyloxy)-1H-indol-6-yl]amino}-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-6-fluorobenzamide was prepared from 2-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzamide (0.25 g, 0.54 mmol) and 2-[6-amino-5-(methyloxy)-2,3-dihydro-1H-indol-1-yl]-N,N-dimethylacetamide (0.16 g, 0.64 mmol) to afford the title compound (0.016 g, 6% over 3 steps) as a grey solid. LCMS (ESI+) and 1H NMR indicate oxidation of the indoline to the indole. ESIMS (M+H)+=517. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.78 (s, 3 H) 2.98 (s, 3 H) 3.80 (s, 3 H) 4.93 (s, 2 H) 6.19-6.20 (m, 1 H) 6.29-6.30 (m, 1 H) 6.82-6.91 (m, 1 H), 6.94-7.01 (m, 1 H) 7.04-7.11 (m, 2 H) 7.25-7.35 (m, 1 H) 7.60 (s, 1 H) 7.98 (s, 1 H) 8.04 (s, 1H) 8.09 (s, 1 H) 8.45 (d, J=8.42 Hz, 1 H) 10.48 (s, 1 H) 11.23 (s, 1 H).

Sources & evidence

ORD record
ord-6d52027d8c084e65b1884a924630d04a
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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