4-methyl-1H-indol-5-amine → HCID 66779293, compound

HRID 1470375Notes

Reaction equation

HRID 1470375 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[CH:20]=[CH:19][C:14]4[O:15][CH2:16][CH2:17][O:18][C:13]=4[CH:12]=3)[O:10][C:3]=12.[CH3:21][C:22]1[C:30]([NH2:31])=[CH:29][CH:28]=[C:27]2[C:23]=1[CH:24]=[CH:25][NH:26]2>>[O:15]1[C:14]2[CH:19]=[CH:20][C:11]([C:9]3[O:10][C:3]4[C:4](=[N:5][CH:6]=[CH:7][C:2]=4[NH:31][C:30]4[C:22]([CH3:21])=[C:23]5[C:27](=[CH:28][CH:29]=4)[NH:26][CH:25]=[CH:24]5)[CH:8]=3)=[CH:12][C:13]=2[O:18][CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 154344964-methyl-1H-indol-5-amineHCID 66779645HCID 66779645, compound

Product 1

HCID 66779293HCID 66779293, compound

Procedure

The title compound was prepared by procedure E using 7-chloro-2-(2,3-dihydro-1,4-benzodioxin-6-yl)furo[3,2-b]pyridine (28.50 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 (15.21 mg; 0.10 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 (22 mg, 55%). (HPLC (method F): 96%, RT: 3.96 min); 1H NMR (500 MHz, DMSO-d6) δ [ppm] 11.15 (s, 1H), 8.52 (s, 1H), 7.92 (d, J=5.5, 1H), 7.54 (d, J=1.8, 1H), 7.46 (d, J=8.5, 1H), 7.41-7.34 (m, 1H), 7.34-7.26 (m, 2H), 6.98 (dd, J=14.6, 8.5, 2H), 6.51 (s, 1H), 6.05 (d, J=5.4, 1H), 4.31 (s, 4H), 2.36 (s, 3H); MS (m/z) 398 [M+H]+, RT: 3.9 min.

Sources & evidence

ORD record
ord-71d53277ba244cacade064a0b455d480
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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