3-aMino-2-naphthaMide → 3-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-2-naphthalenecarboxamide

HRID 1014411

Reaction equation

HRID 1014411 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]=2[N:7]=1.[NH2:22][C:23]1[C:24]([C:33]([NH2:35])=[O:34])=[CH:25][C:26]2[C:31]([CH:32]=1)=[CH:30][CH:29]=[CH:28][CH:27]=2>CO>[Cl:1][C:2]1[N:3]=[C:4]([NH:22][C:23]2[C:24]([C:33]([NH2:35])=[O:34])=[CH:25][C:26]3[C:31]([CH:32]=2)=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:5]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 124714773-aMino-2-naphthaMideHCID 534868282,4-dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 866441803-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-2-naphthalenecarboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using General Protocol II (but using methanol in place of dimethylether) and starting with 2,4-dichloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine (2.5 g, 13.2 mmol) and 3-amino-2-naphthalenecarboxamide (3.00 g, 8.8 mmol), 3-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-2-naphthalenecarboxamide was isolated as a white solid (2.56 g, 59% Yield); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.35 (s, 3 H), 6.69 (d, J=4.03 Hz, 1 H), 7.42-7.51 (m, 3 H), 7.58 (t, J=7.51 Hz, 1 H), 7.72 (d, J=4.03 Hz, 1 H), 7.78-7.85 (m, 2 H), 7.90 (d, J=8.06 Hz, 1 H), 7.97 (d, J=8.42 Hz, 2 H), 8.40 (s, 2 H), 8.69 (s, 1 H), 11.90 (s, 1 H).

Sources & evidence

ORD record
ord-bf7fd1e556ff496f87624c394a12faf2
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Linked notes

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