2-Bromoethyl methyl ether → 3-Chloro-2-{5-chloro-2-[12-(2-methoxy-ethyl)-12-aza-tricyclo[7.2.1.02,7]dodeca-2(7),3,5-trien-4-ylamino]-pyrimidin-4-ylamino}-N-methyl-benzamide

HRID 1040630Notes

Reaction equation

[CH:1]12[NH:12][CH:9]([CH2:10][CH2:11]1)[CH2:8][C:7]1[CH:6]=[CH:5][C:4]([NH:13][C:14]3[N:19]=[C:18]([NH:20][C:21]4[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:22]=4[C:23]([NH:25][CH3:26])=[O:24])[C:17]([Cl:32])=[CH:16][N:15]=3)=[CH:3][C:2]2=1.Br[CH2:34][CH2:35][O:36][CH3:37]>>[Cl:31][C:30]1[C:21]([NH:20][C:18]2[C:17]([Cl:32])=[CH:16][N:15]=[C:14]([NH:13][C:4]3[CH:5]=[CH:6][C:7]4[CH2:8][CH:9]5[N:12]([CH2:34][CH2:35][O:36][CH3:37])[CH:1]([CH2:11][CH2:10]5)[C:2]=4[CH:3]=3)[N:19]=2)=[C:22]([CH:27]=[CH:28][CH:29]=1)[C:23]([NH:25][CH3:26])=[O:24]

Participants

Reactant 2

HCID 809722-Bromoethyl methyl ether

HCID 66829754HCID 66829754, compound

Product 1

HCID 668297603-Chloro-2-{5-chloro-2-[12-(2-methoxy-ethyl)-12-aza-tricyclo[7.2.1.0*2,7*]dodeca-2(7),3,5-trien-4-ylamino]-pyrimidin-4-ylamino}-N-methyl-benzamideYield 34%

Procedure

Following a procedure analogous to 68a, 2-[2-(12-Aza-tricyclo[7.2.1.0*2,7*]dodeca-2(7),3,5-trien-4-ylamino)-5-chloro-pyrimidin-4-ylamino]-3-chloro-N-methyl-benzamide (60 mg, 0.13 mmol), 1-bromo-2-methoxy-ethane (120 mg, 0.48 mmol) were converted to the title compound as a yellow solid (23 mg, 34%). 1HNMR (400 MHz, DMSO-d6) δ 9.2 (bs, 1H), 9.0 (bs, 1H), 8.3 (m, 1H), 8.1 (s, 1H), 7.7 (d, 1H, J=7.6 Hz), 7.6 (d, 1H, J=7.3 Hz), 7.4 (t, 1H, J=8.1 Hz), 7.1 (s, 1H), 7.0 (m, 1H), 6.7 (m, 1H), 3.6-3.4 (m, 4H), 3.2 (s, 3H), 2.9 (m, 1H), 2.7 (d, 3H, J=4.3 Hz), 2.5-2.4 (m, 2H), 2.2 (m, 1H), 2.1-2.0 (m, 2H), 1.5-1.4 (m, 2H); MS (m/e) 527 (M+1); mp 240-244° C.

Sources & evidence

ORD record: ord-6d0a1e393808479ab8860463a6fe15c6
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552186B2

Reaction notes

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