6,7,8,9-Tetrahydro-5-thia-8-aza-benzocyclohepten-2-ylamine → N-{(1R,2R)-2-[5-chloro-2-(6,7,8,9-tetrahydro-5-thia-8-aza-benzocyclohepten-2-ylamino)-pyrimidin-4-ylamino]-cyclohexyl}-methanesulfonamide

HRID 1687244Notes

Reaction equation

HRID 1687244 reaction equation
[CH:1]1[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][S:11][C:5]=2[CH:4]=[CH:3][C:2]=1[NH2:12].Cl[C:14]1[N:19]=[C:18]([NH:20][C@@H:21]2[CH2:26][CH2:25][CH2:24][CH2:23][C@@H:22]2[NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[C:17]([Cl:32])=[CH:16][N:15]=1>>[Cl:32][C:17]1[C:18]([NH:20][C@@H:21]2[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]2[NH:27][S:28]([CH3:31])(=[O:30])=[O:29])=[N:19][C:14]([NH:12][C:2]2[CH:3]=[CH:4][C:5]3[S:11][CH2:10][CH2:9][NH:8][CH2:7][C:6]=3[CH:1]=2)=[N:15][CH:16]=1

Participants

3

Reactant 2

HCID 578538726,7,8,9-Tetrahydro-5-thia-8-aza-benzocyclohepten-2-ylamineHCID 86633896HCID 86633896, compound

Product 1

HCID 67263720N-{(1R,2R)-2-[5-chloro-2-(6,7,8,9-tetrahydro-5-thia-8-aza-benzocyclohepten-2-ylamino)-pyrimidin-4-ylamino]-cyclohexyl}-methanesulfonamideYield 85%

Procedure

Following the procedure of 2f, 6,7,8,9-tetrahydro-5-thia-8-aza-benzocyclohepten-2-ylamine (0.07 g, 0.00039 mol) and N-[(1S,2R)-2-(2,5-dichloro-pyrimidin-4-ylamino)-cyclohexyl]-methanesulfonamide (0.13 g, 0.00039 mol) were reacted giving N-{(1R,2R)-2-[5-chloro-2-(6,7,8,9-tetrahydro-5-thia-8-aza-benzocyclohepten-2-ylamino)-pyrimidin-4-ylamino]-cyclohexyl}-methanesulfonamide (0.16 g, 85%). MP: 141-3° C.; 1H-NMR (DMSO-d6) 9.30 (s, 1H), 7.93-5 (s, 1H), 7.73-9 (s, 1H), 7.44-6 (d, 1H), 7.33-5 (d, 1H), 7.16-8 (d, 1H), 6.76-8 (d, 1H), 3.91 (s, 1H), 3.84-5 (m, 1H), 3.22-4 (m, 2H), 2.93 (s, 2H), 2.63-4 (m, 2H), 2.00-12 (m, 2H), 1.70 (m, 2H), 1.27-37 (m, 4H); LC/MS (ESI+): 483 (M).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-9c673315ddbe4e988b7680dbe3fe0bf1
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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