Sodium Hydroxide → HCID 70144089, compound

HRID 1281692Notes

Reaction equation

HRID 1281692 reaction equation
C([O:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][C@@H:7]([N:11]2[C:15]3[CH:16]=[C:17]([Cl:21])[C:18]([Cl:20])=[CH:19][C:14]=3[N:13]=[C:12]2Br)[C@@H:6]1[O:23]C(=O)C)(=O)C.[CH:27]1([NH2:30])[CH2:29][CH2:28]1.[OH-].[Na+]>>[Cl:20][C:18]1[C:17]([Cl:21])=[CH:16][C:15]2[N:11]([C@@H:7]3[CH2:8][CH2:9][CH2:10][C@@H:5]([OH:4])[C@H:6]3[OH:23])[C:12]([NH:30][CH:27]3[CH2:29][CH2:28]3)=[N:13][C:14]=2[CH:19]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 69828CyclopropylamineHCID 86585504HCID 86585504, compound

Product 1

HCID 70144089HCID 70144089, compoundYield 76%

Procedure

(±)-(1R*,2S*,3R*)-3-(2-Bromo-5,6-dichloro-1H-benzimidazol-1-yl)-1,2-cyclohexanediyl diacetate (464 mg, 1.00 mmol) and cyclopropylamine were reacted as in example 46. The solution was cooled and 1 N sodium hydroxide (one equivalent) was added. Volatiles were evaporated in vacuo and the residual solid was crystallized from methanol to provide title compound as off-white powder (271 mg, 76%), m.p. >25° C.; 1H-NMR (DMSO-d6, 200 MHz) δ: 7.62, 7.44 (both s, each 1, 2 aromatic CH), 7.00-6.95 (m, 1, NH), 4.66 (d, J=6.2 Hz, 1, OH), 4.56 (d, J=2.7 Hz, 1, OH), 4.3-3.9 (m, 3, 2 OCH and NCH), 2.8-2.65 (m, 1, NCH), 2.1-1.4 (m, 6, 3 CH2), 0.75-0.45 (m, 4, 2 CH2 of cyclopropyl).

Workup

  1. temperatureThe solution was cooled
  2. customVolatiles were evaporated in vacuo
  3. customthe residual solid was crystallized from methanol

Sources & evidence

ORD record
ord-43d70fe85d674fcd963b61d49e9bf5d8
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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