Ethyl 2-chloro-1,3-benzothiazole-6-carboxylate → Ethyl 2-(3-((5-cyclopropyl-3-(2-phenylcyclopropyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)benzo[d]thiazole-6-carboxylate

HRID 1748211Notes

Reaction equation

HRID 1748211 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([CH:9]3[CH2:11][CH:10]3[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:5]=2[CH2:18][O:19][CH:20]2[CH2:26][CH:25]3[N:27]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:22]([CH2:23][CH2:24]3)[CH2:21]2)[CH2:3][CH2:2]1.Cl[C:36]1[S:37][C:38]2[CH:44]=[C:43]([C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH:42]=[CH:41][C:39]=2[N:40]=1>>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([CH:9]3[CH2:11][CH:10]3[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:5]=2[CH2:18][O:19][CH:20]2[CH2:21][CH:22]3[N:27]([C:36]4[S:37][C:38]5[CH:44]=[C:43]([C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH:42]=[CH:41][C:39]=5[N:40]=4)[CH:25]([CH2:24][CH2:23]3)[CH2:26]2)[CH2:3][CH2:2]1.[CH:1]1([C:4]2[O:8][N:7]=[C:6]([CH:9]3[CH2:11][CH:10]3[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:5]=2[CH2:18][O:19][CH:20]2[CH2:26][CH:25]3[N:27]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:22]([CH2:23][CH2:24]3)[CH2:21]2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 12692400Ethyl 2-chloro-1,3-benzothiazole-6-carboxylateHCID 67983745Tert-butyl 3-((5-cyclopropyl-3-(2-phenylcyclopropyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octane-8-carboxylate

Product 2

HCID 67983333Ethyl 2-(3-((5-cyclopropyl-3-(2-phenylcyclopropyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)benzo[d]thiazole-6-carboxylateHCID 67983745Tert-butyl 3-((5-cyclopropyl-3-(2-phenylcyclopropyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octane-8-carboxylate

Procedure

Ethyl 2-(3-((5-cyclopropyl-3-(2-phenylcyclopropyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)benzo[d]thiazole-6-carboxylate (10A) was prepared from tert-butyl 3-((5-cyclopropyl-3-(2-phenylcyclopropyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octane-8-carboxylate and ethyl 2-chlorobenzothiazole-6-carboxylate following the procedure described in the preparation of Example 7. The crude product was purified by silica gel column chromatography with hexane-EtOAc 20% isocratic as eluant to yield the title compound.

Workup

  1. customdescribed in the preparation of Example 7
  2. customThe crude product was purified by silica gel column chromatography with hexane-EtOAc 20% isocratic as eluant

Sources & evidence

ORD record
ord-ca0b9de2c47840d0a006ac0a0f9ee42c
Source dataset
uspto-grants-2015_10
Patent number
US09150568B2

Reaction notes

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