Benzo(d)thiazol-2-amine → tert-butyl 8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 333873Notes

Reaction equation

HRID 333873 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[C:11]([C:18](O)=[O:19])[CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[S:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=[C:22]1[NH2:30].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.ClCCl>[S:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=[C:22]1[NH:30][C:18]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:17][CH2:16]2)=[O:19]

Participants

6

Reactant 3

HCID 8706Benzo(d)thiazol-2-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 450740022-[(Tert-butoxy)carbonyl]-1,2,3,4-tetrahydroisoquinoline-8-carboxylic acid

Product 1

HCID 59447535tert-butyl 8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylic acid (6.7 g), benzo[d]thiazol-2-amine (5.5 g) and 4-dimethylaminopyridine (6.6 g) in dichloromethane (78 mL) were treated with 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (9.3 g) at room temperature overnight. The reaction mixture was diluted with dichloromethane (450 mL) and washed with 3% aqueous HCl, water, and brine. The organic layer was dried over Na2SO4, filtered and concentrated to provide the title compound.

Workup

  1. washwashed with 3% aqueous HCl, water, and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-581d648b006f48cc802c7346f9ebf4dd
Source dataset
uspto-grants-2014_11
Patent number
US08883784B2

Reaction notes

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