12-Aza-tricyclo[7.2.1.0*2,7*]dodeca-2(7),3,5-trien-4-ylamine hydrochloride salt → HCID 66829754, compound

HRID 1040629Notes

Reaction equation

HRID 1040629 reaction equation
Cl.[CH:2]12[NH:13][CH:10]([CH2:11][CH2:12]1)[CH2:9][C:8]1[CH:7]=[CH:6][C:5]([NH2:14])=[CH:4][C:3]2=1.[Cl:15][C:16]1[C:17]([NH:26][C:27]2[C:32]([Cl:33])=[CH:31][N:30]=[C:29](Cl)[N:28]=2)=[C:18]([CH:23]=[CH:24][CH:25]=1)[C:19]([NH:21][CH3:22])=[O:20]>>[CH:2]12[NH:13][CH:10]([CH2:11][CH2:12]1)[CH2:9][C:8]1[CH:7]=[CH:6][C:5]([NH:14][C:29]3[N:28]=[C:27]([NH:26][C:17]4[C:16]([Cl:15])=[CH:25][CH:24]=[CH:23][C:18]=4[C:19]([NH:21][CH3:22])=[O:20])[C:32]([Cl:33])=[CH:31][N:30]=3)=[CH:4][C:3]2=1

Participants

3

Reactant 2

HCID 6726400812-Aza-tricyclo[7.2.1.0*2,7*]dodeca-2(7),3,5-trien-4-ylamine hydrochloride saltHCID 866338732-(2,5-dichloro-pyrimidin-4-ylamino)-3-chloro-N-methyl-benzamide

Product 1

HCID 66829754HCID 66829754, compound

Procedure

Following a procedure analogous to 61e, 12-Aza-tricyclo[7.2.1.0*2,7*]dodeca-2(7),3,5-trien-4-ylamine hydrochloride salt (83 mg, 0.39 mmol) and 3-chloro-2-(2,5-dichloro-pyrimidin-4-ylamino)-N-methyl-benzamide (see Example 312a-b for preparation) (100 mg, 0.30 mmol) were converted to the title compound isolated as an ivory solid (85 mg, 18%). 1HNMR (400 MHz, DMSO-d6) δ 9.2-9.0 (m, 2H), 8.4 (bs, 1H), 8.1 (s, 1H), 7.7 (d, 1H, J=7.3 Hz), 7.6 (d, 1H, J=7.6 Hz), 7.4 (m, 1H), 7.1 (s, 1H), 7.0 (d, 1H, J=7.6 Hz), 6.7 (d, 1H, J=8.1 Hz), 3.8-3.6 (m, 2H), 3.3 (bs, 1H), 2.9 (dd, 1H, J=16.2, 4.3 Hz), 2.6 (s, 3H), 2.3 (d, 1H, J=16.2 Hz), 1.9-1.8 (m, 2H), 1.6-1.4 (m, 2H); MS (m/e) 469 (M+1); mp 150-154° C.

Sources & evidence

ORD record
ord-80dff6b63fae4e73b7e37b6d78ed2dad
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

Loading…