Triethylamine → 1-(6-(1-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)azetidin-3-yl 4-nitrobenzenesulfonate

HRID 2040950Notes

Reaction equation

HRID 2040950 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:20]=[CH:19][C:10]3[N:11]=[C:12]([N:14]4[CH2:17][CH:16]([OH:18])[CH2:15]4)[S:13][C:9]=3[CH:8]=2)[CH:4]=[N:3]1.C(N(CC)C(C)C)(C)C.[N+:30]([C:33]1[CH:38]=[CH:37][C:36]([S:39](N2C=NC=N2)(=[O:41])=[O:40])=[CH:35][CH:34]=1)([O-:32])=[O:31].C(N(CC)CC)C>ClCCl>[N+:30]([C:33]1[CH:34]=[CH:35][C:36]([S:39]([O:18][CH:16]2[CH2:17][N:14]([C:12]3[S:13][C:9]4[CH:8]=[C:7]([C:5]5[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=5)[CH:20]=[CH:19][C:10]=4[N:11]=3)[CH2:15]2)(=[O:41])=[O:40])=[CH:37][CH:38]=1)([O-:32])=[O:31]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81531DiisopropylethylamineHCID 937961-((4-Nitrophenyl)sulfonyl)-1H-1,2,4-triazole2×HCID 669055801-(6-(1-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)azetidin-3-ol

Product 1

HCID 866319061-(6-(1-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)azetidin-3-yl 4-nitrobenzenesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 1-(6-(1-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)azetidin-3-ol (Reference Example 2, 0.143 g, 0.50 mmol), N,N-diisopropylethylamine (0.105 mL, 0.60 mmol), and 1-(4-nitrophenylsulfonyl)-1H-1,2,4-triazole (0.178 g, 0.70 mmol) in dichloromethane (5.0 mL) was stirred a few hours and then triethylamine (0.14 mL, 1.0 mmoL) was added. After the mixture had been stirred overnight additional 1-(4-nitrophenylsulfonyl)-1H-1,2,4-triazole (0.076 g, 0.30 mmol) was added. The mixture was stirred another day and then placed directly onto a column of silica and purified chromatographically (100% CH2Cl2 to 80:20 CH2Cl2/ethyl acetate) to give 1-(6-(1-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)azetidin-3-yl 4-nitrobenzenesulfonate. 1H NMR (300 MHz, CD3OD) δ ppm 3.91 (s, 3H), 4.20-4.25 (m, 2H), 4.46-4.52 (m, 2H), 5.41-5.50 (m, 1H), 7.46 (d, J=8 Hz, 1H), 7.52 (dd, J=1, 8 Hz, 1H), 7.79 (s, 1H), 7.87 (s, 1H), 7.92 (s, 1H), 8.24 (d, J=9 Hz, 2H), 8.51 (d, J=9 Hz, 2H); MS (ESI) m/z 472 (M+H)+.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred another day
  3. custompurified chromatographically (100% CH2Cl2 to 80:20 CH2Cl2/ethyl acetate)

Sources & evidence

ORD record
ord-220e7bf5957b4faa8197fa876e2809a7
Source dataset
uspto-grants-2013_11
Patent number
US08580968B2

Reaction notes

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