Triethylamine → N-[3(S)-5-Cyclohexyl-2,3-dihydro-1-methyl-2-oxo1H-1,4-benzodiazepin-3-yl]N'-[3-(phenylsulphonylaminocarbonyl)phenyl]urea

HRID 2379360Notes

Reaction equation

HRID 2379360 reaction equation
[C:1]1([S:7]([NH:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=2)=[O:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC(Cl)(O[C:24](=[O:30])OC(Cl)(Cl)Cl)Cl.C(N([CH2:37][CH3:38])CC)C.[NH2:39][C@H:40]1[N:46]=[C:45](C2CCCCC2)[C:44]2[CH:53]=[CH:54][CH:55]=[CH:56][C:43]=2[N:42]([CH3:57])[C:41]1=[O:58]>C(OCC)C.O1CCCC1>[CH2:38]1[CH2:37][CH:3]([C@:40]2([NH:39][C:24]([NH:19][C:15]3[CH:16]=[CH:17][CH:18]=[C:13]([C:11]([NH:10][S:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)(=[O:9])=[O:8])=[O:12])[CH:14]=3)=[O:30])[N:46]=[CH:45][C:44]3[CH:53]=[CH:54][CH:55]=[CH:56][C:43]=3[N:42]([CH3:57])[C:41]2=[O:58])[CH2:2][CH2:1][CH2:6]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 184055003-Amino-N-(phenylsulfonyl)benzamideHCID 186560323(S)-amino-5-cyclohexyl-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one

Product 1

HCID 67821677N-[3(S)-5-Cyclohexyl-2,3-dihydro-1-methyl-2-oxo1H-1,4-benzodiazepin-3-yl]N'-[3-(phenylsulphonylaminocarbonyl)phenyl]ureaYield 120.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared in the same way as that described in Example 33, Step 4, using 1-(phenylsulphonylaminocarbonyl)-3-aminobenzene (0.30 g, 1.08 mmol) [Example 14, Step 2]), triphosgene (107 mg, 0.36 mmol), triethylamine (0.45 ml, 3.23 mmol), 3(S)-amino-5-cyclohexyl-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one (0.2 g, 0.74 mmol) and tetrahydrofuran (30 ml). After trituration with diethyl ether, the title compound (248 mg, 59%) was afforded as a colourless solid with >99% e.e. mp 180° C. (dec.). 1H NMR (360 MHz, D6-DMSO) δ 0.82-0.98 (1H, m), 1.08-1.65 (7H, m), 1.75-1.83 (1H, m), 1.88-1.96 (1H, m), 2.90-3.00 (1H, m), 3.31 (3H, s), 5.06 (1H, d, J=8.3 Hz), 7.30-7.36 (2H, m), 7.37-7.41 (2H, m), 7.49-7.56 (2H, m), 7.60-7.65 (3H, m), 7.68-7.76 (2H, m), 7.84 (1H, s), 7.96-7.99 (2H, m), 9.17 (1H, s), 12.46 (1H, brs). [α]D +9.4° (c=0.37, CH3OH).

Workup

  1. customThe title compound was prepared in the same way as

Sources & evidence

ORD record
ord-8bd32a94577d48df8ae024f74fd362c3
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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