4-(1H-pyrazol-1-yl)benzoyl chloride → HCID 72445408, compound

HRID 500402Notes

Reaction equation

HRID 500402 reaction equation
[OH:1][CH:2]1[CH2:20][CH:19]2[N:4]([C:5](=[O:39])[CH:6]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:13][CH:14]3[C:16]([C:22]([NH:24][S:25]([CH:28]4[CH2:30][CH2:29]4)(=[O:27])=[O:26])=[O:23])([NH:17][C:18]2=[O:21])[CH2:15]3)[CH2:3]1.[N:40]1([C:45]2[CH:53]=[CH:52][C:48]([C:49](Cl)=[O:50])=[CH:47][CH:46]=2)[CH:44]=[CH:43][CH:42]=[N:41]1>>[N:40]1([C:45]2[CH:53]=[CH:52][C:48]([C:49]([O:1][CH:2]3[CH2:20][CH:19]4[N:4]([C:5](=[O:39])[CH:6]([NH:31][C:32]([O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[O:33])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:13][CH:14]5[C:16]([C:22]([NH:24][S:25]([CH:28]6[CH2:30][CH2:29]6)(=[O:27])=[O:26])=[O:23])([NH:17][C:18]4=[O:21])[CH2:15]5)[CH2:3]3)=[O:50])=[CH:47][CH:46]=2)[CH:44]=[CH:43][CH:42]=[N:41]1

Participants

3

Reactant 2

HCID 27764744-(1H-pyrazol-1-yl)benzoyl chlorideHCID 68797769tert-butyl N-[4-(cyclopropylsulfonylcarbamoyl)-18-hydroxy-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-en-14-yl]carbamate

Product 1

HCID 72445408HCID 72445408, compoundYield 7.7%

Procedure

Prepared by way of method I using 18-hydroxy-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]-nonadec-7-ene (100 mg, 0.175 mmol) and 4-(1-pyrazolyl)benzoyl chloride (183 mg, 0.88 mmol). The final trituration (diethyl ether/hexane) and filtration gave 10 mg (7.7%) of 18-(4-[1-pyrazolyl]benzoyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diazatricyclo-[14.3.0.04,6]-nonadec-7-ene as a white powder: 99.9% pure (HPLC), MS m/z 737 (M−H)−, HRMS: calcd. 739.3125 and found 739.3109 (M+H)+, mp 167-169° C.

Workup

  1. customPrepared by way of method I
  2. filtrationThe final trituration (diethyl ether/hexane) and filtration

Sources & evidence

ORD record
ord-03820dcd82bc4a67b7ba526985782524
Source dataset
uspto-grants-2010_08
Patent number
US07772183B2

Reaction notes

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