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

HRID 588670Notes

Reaction equation

HRID 588670 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[C:11]([C:18]([OH:20])=O)[CH:12]=[CH:13][CH:14]=2)[CH:9]1[CH3:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[S:62]1[C:66]2[CH:67]=[CH:68][CH:69]=[CH:70][C:65]=2[N:64]=[C:63]1[NH2:71]>ClCCl.C(OCC)(=O)C>[S:62]1[C:66]2[CH:67]=[CH:68][CH:69]=[CH:70][C:65]=2[N:64]=[C:63]1[NH:71][C:18]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[CH:9]([CH3:21])[N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:17][CH2:16]2)=[O:20]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8706Benzo(d)thiazol-2-amineHCID 2724699PyBOPHCID 866812642-(Tert-butoxycarbonyl)-1-methyl-1,2,3,4-tetrahydroisoquinoline-8-carboxylic acid

Product 1

HCID 89498397tert-butyl 8-(benzo[d]thiazol-2-ylcarbamoyl)-1-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of EXAMPLE 43A (400 mg), PyBOP (benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate, 714 mg), triethylamine (0.383 mL) and benzo[d]thiazol-2-amine (247 mg) in dichloromethane (10 mL) was stirred overnight at room temperature. The mixture was diluted with ethyl acetate (100 mL), washed with brine (30 mL×3), dried over Na2SO4, filtered, concentrated and purified by flash chromatography (silica gel, petroleum ether/ethyl acetate=1/1).

Workup

  1. washwashed with brine (30 mL×3)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography (silica gel, petroleum ether/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-e4222337b4ad4fd38f9e669dfcb51c8b
Source dataset
uspto-grants-2016_01
Patent number
US09227963B2

Reaction notes

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