Iodoethane → HCID 67264298, compound

HRID 1686941Notes

Reaction equation

HRID 1686941 reaction equation
[Cl:1][C:2]1[C:3]([NH:23][C@@H:24]2[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]2[NH:30][S:31]([CH3:34])(=[O:33])=[O:32])=[N:4][C:5]([NH:8][C:9]2[CH:19]=[CH:18][C:17]3[CH2:16][CH:15]4[NH:20][CH:12]([CH2:13][CH2:14]4)[C:11]=3[C:10]=2[O:21][CH3:22])=[N:6][CH:7]=1.I[CH2:36][CH3:37]>>[Cl:1][C:2]1[C:3]([NH:23][C@@H:24]2[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]2[NH:30][S:31]([CH3:34])(=[O:33])=[O:32])=[N:4][C:5]([NH:8][C:9]2[CH:19]=[CH:18][C:17]3[CH2:16][CH:15]4[N:20]([CH2:36][CH3:37])[CH:12]([CH2:13][CH2:14]4)[C:11]=3[C:10]=2[O:21][CH3:22])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 6340IodoethaneHCID 67264393HCID 67264393, compound

Product 1

HCID 67264298HCID 67264298, compoundYield 23%

Procedure

Following a procedure analogous to 68a, N-{(1R,2R)-2-[5-Chloro-2-(3-methoxy-12-aza-tricyclo[7.2.1.0*2,7*]dodeca-2(7),3,5-trien-4-ylamino)-pyrimidin-4-ylamino]-cyclohexyl}-methanesulfonamide (25 mg, 0.049 mmol), iodoethane were converted to the title compound as a light pink solid (6 mg, 23%), as a mixture of diastereomers. 1HNMR (400 MHz, CDCl3) δ 7.9 (s, 1H), 7.7 (m, 1H), 7.4 (m, 1H), 7.2 (m, 1H), 5.7 (m, 1H), 3.8 (m, 1H), 3.7 (m, 1H), 3.5 (s, 3H), 3.3-3.0 (m, 3H), 2.9 (s, 3H), 2.8 (m, 1H), 2.6 (m, 1H), 2.2-1.8 (m, 9H), 1.7-1.6 (m, 3H), 1.4-1.2 (m, 1H), 1.1-1.0 (m, 4H); MS (m/e) 535 (M+1); mp 102-106° C.

Sources & evidence

ORD record
ord-d4c6f167aff04161b9b26b128163e4fb
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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