Ethanol → HCID 178488057, compound

HRID 2367393Notes

Reaction equation

HRID 2367393 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10](F)[CH:9]=2)[CH:5]=[C:4]([N:17]2[CH2:22][CH2:21]O[CH:19]([C:23]3[NH:27][C:26]4[CH:28]=[CH:29][C:30](OC)=[CH:31][C:25]=4[N:24]=3)[CH2:18]2)[N:3]=1.[OH2:34].[NH2:35][NH2:36].[OH2:37].[CH2:38](O)C>>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]3[C:11]([C:12]([NH2:13])=[N:35][NH:36]3)=[CH:14][CH:15]=2)[CH:5]=[C:4]([N:17]2[CH2:22][CH2:21][O:34][CH:19]([C:23]3[NH:24][C:25]4[CH:31]=[CH:30][C:29]([O:37][CH3:38])=[CH:28][C:26]=4[N:27]=3)[CH2:18]2)[N:3]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 178488058HCID 178488058, compound

Product 1

HCID 178488057HCID 178488057, compound

Procedure

To a suspension of 4-(2-amino-6-{2-[5-(methyloxy)-1H-benzimidazol-2-yl]-4-morpholinyl}-4-pyrimidinyl)-2-fluorobenzonitrile (340 mg, 0.763 mmol) in ethanol (8 mL) at room temperature was added hydrazine hydrate (764 mg, 15.27 mmol). The reaction vessel was sealed and heated in CEM Discover using initial high to 120° C. for 1 hour. After cooling, the reaction was poured into water. The resulting precipitate was filtered and dried under vacuum to afford the title compound (148 mg). LC-MS (ES) m/z=458 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 3.21-3.10 (m, 2H), 3.82-3.78 (m, 4H), 4.11 (d, 1H), 4.34 (d, 1H), 4.86-4.77 (m, 2H), 5.39 (bs, 2H), 6.23 (bs, 2H), 6.71 (s, 1H), 6.85-6.78 (m, 1H), 7.14-6.95 (m, 1H), 7.50-7.34 (m, 1H), 7.61 (d, 1H), 7.71 (d, 1H), 7.99 (s, 1H), 11.53 (s, 1H), 12.43 (s, 1H).

Workup

  1. customThe reaction vessel was sealed
  2. temperatureheated in CEM Discover
  3. customhigh to 120° C.
  4. customfor 1 hour
  5. temperatureAfter cooling
  6. filtrationThe resulting precipitate was filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-746ff03ac80449849abb1319d7530e7c
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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