Triethylamine → HCID 11646002, compound

HRID 408524Notes

Reaction equation

HRID 408524 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:12]([OH:14])=O)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[C:15]1([C:21]2[N:22]=[C:23]([NH2:26])[S:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(#N)C>[C:15]1([C:21]2[N:22]=[C:23]([NH:26][C:12]([C:9]3([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)[CH2:10][CH2:11]3)=[O:14])[S:24][CH:25]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 403022-Amino-4-phenylthiazoleHCID 855751-(4-Methoxyphenyl)cyclopropane-1-carboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 11646002HCID 11646002, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(4-Methoxy-phenyl)-cyclopropanecarboxylic acid (2.18 g, 11.4 mmol) and 4-phenyl-thiazol-2-ylamine (2.00 g, 11.4 mmol) were dissolved in acetonitrile (50 mL) containing triethylamine (3.17 mL, 22.8 mmol). Benzotriazol-1-yloxy tris(dimethylamino)-phosphonium hexafluorophosphate (BOP, 4.95 g, 11.4 mmol) was added and the solution was allowed to stir for 64 hours. The reaction mixture was evaporated to dryness and purified by column chromatography on silica gel using a gradient of 5-20% ethyl acetate in hexanes. The pure fractions were combined and evaporated to dryness to yield a white solid (1.9 g, 5.43 mmol, 47.5%). ESI-MS m/z calc. 350.1. found 351.1 (M+1)+. Retention time of 3.68 minutes. 1H NMR (400 MHz, CD3CN) δ 1.27 (q, J=3.6 Hz, 2H), 1.66 (q, J=3.6 Hz, 2H), 3.87 (s, 3H), 7.04 (m, 2H), 7.40 (m, 6H), 7.82 (m, 2H), 8.79 (s, 1H).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. custompurified by column chromatography on silica gel using a gradient of 5-20% ethyl acetate in hexanes
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-2d06ef28640045d79a67ac94dd9784fc
Source dataset
uspto-grants-2014_06
Patent number
US08759335B2

Reaction notes

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