Diisopropylethylamine → HCID 68859320, compound

HRID 1726432Notes

Reaction equation

HRID 1726432 reaction equation
Cl.C([O:4][C:5]([C:7]12[CH2:25][CH:24]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:16]([NH2:26])[C:15](=[O:27])[N:14]1[CH:10]([CH2:11][CH:12]([O:28][C:29]([N:31]3[CH2:40][CH2:39][C:38]4[C:33](=[C:34](C(F)(F)F)[CH:35]=[CH:36][CH:37]=4)[CH2:32]3)=[O:30])[CH2:13]1)[C:9](=[O:45])[NH:8]2)=[O:6])C.C(N(C(C)C)CC)(C)C.[CH:55]1([N:60]=[C:61]=[O:62])[CH2:59][CH2:58][CH2:57][CH2:56]1>ClCCl>[CH:55]1([NH:60][C:61](=[O:62])[NH:26][C@@H:16]2[C:15](=[O:27])[N:14]3[C@@H:10]([CH2:11][C@@H:12]([O:28][C:29]([N:31]4[CH2:40][CH2:39][C:38]5[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=5)[CH2:32]4)=[O:30])[CH2:13]3)[C:9](=[O:45])[NH:8][C@@:7]3([C:5]([OH:4])=[O:6])[C@@H:24]([CH2:25]3)[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:59][CH2:58][CH2:57][CH2:56]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 643500Cyclopentyl IsocyanateHCID 66657120HCID 66657120, compound

Product 1

HCID 68859320HCID 68859320, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

14-Amino-2,15-dioxo-18-(8-trifluoromethyl-3,4-dihydro-1H-isoquinoline-2-carbonyloxy)-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid ethyl ester hydrochloride salt (49 mg, 74 umol), diisopropylethylamine (29 mg, 222 umol), and cyclopentyl isocyanate (25 mg, 222 umol) were taken up in 375 uL dichloromethane and stirred at 19 C for 1 hour. The reaction was loaded directly onto a C18 flash column and eluted with water/acetonitrile (10 to 100%) containing 0.1% TFA to provide the title product as a white solid (42 mg, 77%). MS m/z 732.2 (MH+).

Workup

  1. washeluted with water/acetonitrile (10 to 100%)
  2. additioncontaining 0.1% TFA

Sources & evidence

ORD record
ord-886317e925e5456f92b313e92a1c0d84
Source dataset
uspto-grants-2009_02
Patent number
US07491794B2

Reaction notes

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