Oxane-4-carboxylic acid → HCID 178523746, compound

HRID 2042426Notes

Reaction equation

HRID 2042426 reaction equation
Cl.Cl.Cl.[S:4]1[C:12]2[CH:11]=[CH:10][N:9]=[C:8]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C@H:21]4[CH2:26][CH2:25][C@H:24]([NH2:27])[CH2:23][CH2:22]4)[CH2:15][CH2:14]3)[C:7]=2[CH:6]=[CH:5]1.[O:28]1[CH2:33][CH2:32][CH:31]([C:34](O)=[O:35])[CH2:30][CH2:29]1>>[S:4]1[C:12]2[CH:11]=[CH:10][N:9]=[C:8]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C@H:21]4[CH2:26][CH2:25][C@H:24]([NH:27][C:34]([CH:31]5[CH2:32][CH2:33][O:28][CH2:29][CH2:30]5)=[O:35])[CH2:23][CH2:22]4)[CH2:15][CH2:14]3)[C:7]=2[CH:6]=[CH:5]1

Participants

3

Reactant 2

HCID 219302Oxane-4-carboxylic acidHCID 178478593HCID 178478593, compound2×

Product 1

HCID 178523746HCID 178523746, compound

Procedure

The title compound was prepared in analogy to example 4 starting from trans-4-[2-(4-thieno[3,2-e]pyridin-4-yl-piperazin-1-yl)-ethyl]-cyclohexylamine trihydrochloride (intermediate B) (150 mg, 0.33 mmol) and tetrahydropyran-4-ylcarboxylic acid (45 mg, 0.34 mmol). Purification by flash chromatography on silica gel (CH2Cl2/MeOH 95:5). White crystals (51 mg, 34%), MS (ISP) m/z=457.3 [(M+H)+].

Workup

  1. customPurification by flash chromatography on silica gel (CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-44fd4ce3c1ba4bd9a01377e1940d2ff6
Source dataset
uspto-grants-2013_11
Patent number
US08586579B2

Reaction notes

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