Carbamate → HCID 22283296, compound

HRID 2308476Notes

Reaction equation

HRID 2308476 reaction equation
Cl[CH2:2][C:3]1[CH:28]=[CH:27][C:6]([C:7]([NH:9][C:10]2[S:11][C:12]3[C:18]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[CH:17][CH:16]=[C:15]([O:25][CH3:26])[C:13]=3[N:14]=2)=[O:8])=[CH:5][CH:4]=1.C([N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1)(OC(C)(C)C)=O.C(=O)([O-])N.C(=O)([O-])[O-].[Na+].[Na+]>FC(F)(F)C(O)=O>[CH3:26][O:25][C:15]1[C:13]2[N:14]=[C:10]([NH:9][C:7](=[O:8])[C:6]3[CH:5]=[CH:4][C:3]([CH2:2][N:36]4[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]4)=[CH:28][CH:27]=3)[S:11][C:12]=2[C:18]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 276CarbamateHCID 10340Sodium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 22283106HCID 22283106, compound

Product 1

HCID 22283296HCID 22283296, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Conversion of 4-cloromethyl-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-benzamide (84 mg, 0.20 mmol) with 1-BOC-piperazine (372 mg, 1.9 mmol) using the general procedure C and afterwards cleavage of the neat carbamate in trifluoroacetic acid (1 ml) followed by saturated aqueous sodium carbonate affords the product as colorless crystals in 72% yield. MS: m/e=468 (M+H+).

Sources & evidence

ORD record
ord-9f9e2d4f45a84bb09e2a525d6ceec792
Source dataset
uspto-grants-2004_12
Patent number
US06835732B2

Reaction notes

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