Imidazole → HCID 58346545, compound

HRID 222053Notes

Reaction equation

HRID 222053 reaction equation
CS(O[CH2:6][CH2:7][N:8]1[C:16]2[CH2:15][CH2:14][C:13]3[C:17]4[C:23]([NH:24][C:25]5[CH:26]=[C:27]6[C:31](=[CH:32][CH:33]=5)[N:30]([CH2:34][C:35]5[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[CH:36]=5)[N:29]=[CH:28]6)=[N:22][CH:21]=[N:20][C:18]=4[S:19][C:12]=3[C:11]=2[CH:10]=[N:9]1)(=O)=O.[NH:42]1[CH:46]=[CH:45][N:44]=[CH:43]1.C(N(C(C)C)CC)(C)C>>[F:41][C:37]1[CH:36]=[C:35]([CH:40]=[CH:39][CH:38]=1)[CH2:34][N:30]1[C:31]2[C:27](=[CH:26][C:25]([NH:24][C:23]3[N:22]=[CH:21][N:20]=[C:18]4[S:19][C:12]5[C:11]6[CH:10]=[N:9][N:8]([CH2:7][CH2:6][N:42]7[CH:46]=[CH:45][N:44]=[CH:43]7)[C:16]=6[CH2:15][CH2:14][C:13]=5[C:17]=34)=[CH:33][CH:32]=2)[CH:28]=[N:29]1

Participants

4

Reactant 3

HCID 795ImidazoleHCID 81531DiisopropylethylamineHCID 58346423HCID 58346423, compound

Product 1

HCID 58346545HCID 58346545, compound

Procedure

The title compound was prepared following the procedure described for example 277, utilizing 2-(6-{[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino}-4,5-dihydro-3H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazol-3-yl)ethyl methanesulfonate (1.53 g, 3.0 mmol), imidazole (17 mg, 0.25 mmol), and diisopropylethylamine (0.06 mL, 0.34 mmol). The desired product was collected as a white solid (37 mg, 39%). 1H-NMR (CD2Cl2-d2) δ 8.26 (s, 1H), 8.04 (s, 1H), 7.98 (s, 1H), 7.65 (s, 1H), 7.50 (d, 1H), 7.40 (d, 1H), 7.21-7.38 (m, 2H), 6.90-7.00 (m, 3H), 6.82 (dd, 1H), 6.72 (s, 1H), 5.60 (s, 2H), 4.42 (t, 2H), 4.35 (t, 2H), 3.17 (t, 2H), 2.40 (t, 2H); LCMS RT=2.58 min; [M+H]+=562.4

Workup

  1. customThe desired product was collected as a white solid (37 mg, 39%)

Sources & evidence

ORD record
ord-c9622d2d8dc84c448e582e2a9381b162
Source dataset
uspto-grants-2012_06
Patent number
US08207172B2

Reaction notes

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