Triethylamine → {2-[(2-Amino-benzothiazole-6-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester

HRID 416240

Reaction equation

HRID 416240 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]([OH:13])=O)[CH:8]=[CH:7][C:5]=2[N:6]=1.[C:14]([O:18][C:19](=[O:28])[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[NH2:27])([CH3:17])([CH3:16])[CH3:15].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(CC)CC>CN(C=O)C>[C:14]([O:18][C:19](=[O:28])[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[NH:27][C:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([NH2:1])[S:3][C:4]=2[CH:10]=1)=[O:13])([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 667406-Benzothiazolecarboxylic acid, 2-amino-HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamine

Product 1

HCID 58930649{2-[(2-Amino-benzothiazole-6-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl esterYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The acid 114 (1.80 g, 9.27 mmol) was combined with (2-amino-phenyl)-carbamic acid tert-butyl ester (2.31 g, 11.1 mmol) and BOP (4.91 g, 11.1 mmol) in DMF. To this solution Et3N (5.16 ml, 37.1 mmol) was added and the mixture was stirred overnight at room temperature under nitrogen, concentrated in vacuo and purified by flash column chromatography (30% hexane/EtOAc). To further purify the product, the mixture was partitioned between EtOAc and water, organic layer was separated, dried over MgSO4 and evaporated give the title compound 115 (1.84 g, 52%). 1H-NMR (DMSO) δ: 9.72 (s, 1H), 8.66 (m, 1H); 8.22 (d, J=1.8 Hz, 1H); 7.80 (m, 3H); 7.50 (m, 2H); 7.37 (m, 1H); 7.14 (m, 2H); 1.44 (s, 9H).

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by flash column chromatography (30% hexane/EtOAc)
  3. customTo further purify the product
  4. customthe mixture was partitioned between EtOAc and water, organic layer
  5. customwas separated
  6. dry with materialdried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-43b2456e5de046fb85e66de78ee4d9a1
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Linked notes

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