Methylamine → HCID 59442082, compound

HRID 1014465Notes

Reaction equation

HRID 1014465 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:44][CH3:45])=[C:10]([NH:13][C:14]3[N:15]=[C:16]([NH:33][C:34]4[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[C:35]=4[C:36]([NH2:38])=[O:37])[C:17]4[CH:22]=[CH:21][N:20]([S:23]([C:26]5[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=5)(=[O:25])=[O:24])[C:18]=4[N:19]=3)[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH3:46]N>C1COCC1>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:44][CH3:45])=[C:10]([NH:13][C:14]3[N:15]=[C:16]([NH:33][C:34]4[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[C:35]=4[C:36]([NH:38][CH3:46])=[O:37])[C:17]4[CH:22]=[CH:21][N:20]([S:23]([C:26]5[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=5)(=[O:25])=[O:24])[C:18]=4[N:19]=3)[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 59441879HCID 59441879, compound

Product 1

HCID 59442082HCID 59442082, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The remaining half of the reaction mixture from the preparation of 2-({2-{[1-acetyl-5-(methyloxy)-2,3-dihydro-1H-indol-6-yl]amino}-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzamide was diluted with THF (100 mL) and a solution of methylamine (2M, 9 mL), 18 mmol). The reaction mixture was stirred overnight, then concentrated to dryness. The residue was sonicated in CH2Cl2 (15 mL) and filtered. The filtrate was purified by silica gel chromatography using 10% THF/CH2Cl2 to obtain 2-({2-{[1-acetyl-5-(methyloxy)-2,3-dihydro-1H-indol-6-yl]amino}-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluoro-N-methylbenzamide as a yellow solid (236 mg, 41% for 2 steps). 1H NMR (400 MHz, DMSO-d5) δ ppm 2.16 (s, 3H), 2.34 (s, 3H), 2.75 (d, J=4.4 Hz, 3H), 3.19 (d, J=8.24 Hz, 2H), 3.73 (s, 3H), 4.15 (d, J=8.33 Hz, 2H), 6.55 (d, J=3.85 Hz, 1H), 6.94 (t, J=9.25 Hz, 1H), 7.04 (s, 1H), 7.17-7.41 (m, 4H), 7.93 (d, J=8.24 Hz, 2H), 7.98 (J=8.42 Hz, 1H), 8.16 (s, 1H), 8.19 (s, 1H), 8.36-8.52 (m, 1H), 10.16 (s, 1H); ESIMS (M+H)+=644.20.

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was sonicated in CH2Cl2 (15 mL)
  3. filtrationfiltered
  4. customThe filtrate was purified by silica gel chromatography

Sources & evidence

ORD record
ord-35a984345e58421d96219e40f59d0a31
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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