Diisopropylethylamine → HCID 67268639, compound

HRID 251750Notes

Reaction equation

HRID 251750 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:33]1[NH2+:34][C:35]([C:38]2[CH:47]=[CH:46][C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH:39]=2)=[CH:36][N:37]=1)[NH:17]C(=O)CC1C2C(=CC=C(OC)C=2)NC=1C)([OH:10])=[O:9].CCN(C(C)C)C(C)C.[CH3:57][N:58]([CH3:63])[S:59](Cl)(=[O:61])=[O:60]>CN(C=O)C>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:33]1[NH:34][C:35]([C:38]2[CH:47]=[CH:46][C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH:39]=2)=[CH:36][NH+:37]=1)[NH:17][S:59]([N:58]([CH3:63])[CH3:57])(=[O:61])=[O:60])([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 87331357HCID 87331357, compound

Product 1

HCID 67268639HCID 67268639, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 107, 15 (1 eq.), DIPEA (2 eq.) and dimethylsulfamoyl chloride (2 eq.) in DMF was stirred overnight at RT. The crude was purified by preparative RP-HPLC, using H2O (0.1% TFA) and MeCN (+0.1% TFA) as eluents (column: C18) and the desired fractions were lyophilized to afford the titled compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ: 12.04 (1H, bs), 8.33 (1H, s), 8.12 (1H, bs), 8.09-8.00 (2H, m), 7.99-7.87 (3H, m), 7.63-7.52 (2H, m), 4.62-4.51 (1H, m), 2.63 (6H, s), 2.19 (2H, t, J=7.2 Hz), 2.02-1.84 (2H, m), 1.55-1.44 (2H, m), 1.44-1.35 (1H, m), 1.35-1.16 (3H, m). MS (ES) C22H28N4O4S requires: 444, found: 445 (M+H)+.

Workup

  1. customThe crude was purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-c271b0ecd12b4ac09099d4dbd44b8215
Source dataset
uspto-grants-2011_01
Patent number
US07863294B2

Reaction notes

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