4-methyl-1H-indol-5-amine → HCID 66779727, compound

HRID 1470378Notes

Reaction equation

HRID 1470378 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[C:12]([CH3:17])=[N:13][O:14][C:15]=3[CH3:16])[O:10][C:3]=12.[CH3:18][C:19]1[C:27]([NH2:28])=[CH:26][CH:25]=[C:24]2[C:20]=1[CH:21]=[CH:22][NH:23]2>>[CH3:17][C:12]1[C:11]([C:9]2[O:10][C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[NH:28][C:27]3[C:19]([CH3:18])=[C:20]4[C:24](=[CH:25][CH:26]=3)[NH:23][CH:22]=[CH:21]4)[CH:8]=2)=[C:15]([CH3:16])[O:14][N:13]=1

Participants

3

Reactant 2

HCID 154344964-methyl-1H-indol-5-amineHCID 66779649HCID 66779649, compound

Product 1

HCID 66779727HCID 66779727, compound

Procedure

The title compound was prepared by procedure E using 7-chloro-2-(3,5-dimethylisoxazol-4-yl)furo[3,2-b]pyridine (25.10 mg; 0.10 mmol; 1.00 eq.) instead of 7-chloro-2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridine, and 4-methyl-1H-indol-5-ylamine (15.49 mg; 0.11 mmol; 1.05 eq.) instead of 6-amino-2,2-difluoro-4H-benzo[1,4]oxazin-3-one, and was obtained as a beige solid (19 mg, 52%). (HPLC (method F): 99%, RT: 3.49 min); 1H NMR (500 MHz, DMSO-d6) δ [ppm] 11.13 (s, 1H), 8.49 (s, 1H), 7.98 (d, J=5.5, 1H), 7.37 (t, J=2.7, 1H), 7.29 (d, J=8.5, 1H), 7.07 (s, 1H), 6.99 (d, J=8.4, 1H), 6.51 (s, 1H), 6.17 (d, J=5.5, 1H), 2.52 (s, 3H), 2.37 (s, 3H), 2.34 (s, 3H); MS (m/z) 359 [M+H]+, RT: 3.4 min.

Sources & evidence

ORD record
ord-621ef9ab136941a6939b0710ed5056b7
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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