Diisopropylethylamine → HCID 86700404, compound

HRID 879590Notes

Reaction equation

HRID 879590 reaction equation
Br[C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:9]([C@H:18]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:8]([CH3:29])=[CH:7][C:5]=2[N:6]=1.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2([CH3:43])[O:42][CH2:41][CH2:40][NH:39][CH2:38]2)=[CH:33][CH:32]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[C:25]([O:24][C@@H:18]([C:9]1[C:8]([CH3:29])=[CH:7][C:5]2[N:6]=[C:2]([N:39]3[CH2:40][CH2:41][O:42][C:37]([C:34]4[CH:35]=[CH:36][C:31]([Cl:30])=[CH:32][CH:33]=4)([CH3:43])[CH2:38]3)[S:3][C:4]=2[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20])([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 30660432-(4-chlorophenyl)-2-methylmorpholineHCID 86700141(S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

Product 1

HCID 86700404HCID 86700404, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate, 2-(4-chlorophenyl)-2-methylmorpholine and iPr2NEt (20.1 mg, 0.156 mmol) in DMF was heated at 100° C. for 10 hours. The mixture was evaporated to dryness and separated on CombiFlash, eluting with 0-70% EtOAc/Hex to give title compound. LCMS-ESI+: calc'd for C33H36Cl2N2O4S: 627.2, 629.2 (M+H+); found: 627.3, 629.3 (M+H+).

Workup

  1. customThe mixture was evaporated to dryness
  2. customseparated on CombiFlash
  3. washeluting with 0-70% EtOAc/Hex

Sources & evidence

ORD record
ord-bc6bc37aeb9243a59f4ef03b9f09fd2a
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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