Methanol → HCID 131728493, compound

HRID 1172523Notes

Reaction equation

HRID 1172523 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:9][CH2:10][N:11]([CH2:34][CH2:35]Cl)[C:12]1[CH:32]=[C:31]([Cl:33])[C:15]2[O:16][C:17]3[C:26]([CH3:27])=[CH:25][C:24]([C:28]([OH:30])=[O:29])=[CH:23][C:18]=3[S:19](=[O:22])(=[O:21])[CH2:20][C:14]=2[CH:13]=1.[CH3:37]O>>[CH3:37][O:30][C:28]([C:24]1[CH:25]=[C:26]([CH3:27])[C:17]2[O:16][C:15]3[C:31]([Cl:33])=[CH:32][C:12]([N:11]4[CH2:10][CH2:9][N:7]([CH:1]5[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]5)[CH2:35][CH2:34]4)=[CH:13][C:14]=3[CH2:20][S:19](=[O:21])(=[O:22])[C:18]=2[CH:23]=1)=[O:29]

Participants

4

Reactant 3

HCID 887MethanolHCID 7965CyclohexylamineHCID 1317284742-[Bis-(2-chloroethyl)amino]-4-chloro-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]-cycloheptene-8-carboxylic acid

Product 1

HCID 131728493HCID 131728493, compound

Procedure

Cyclohexylamine (0.7 mL 6.25 mmol) was added to a solution of Example 102j (0.6 g, 1.25 mmol) in methanol (10 mL), followed by the addition of n-tetrabutylammonium iodide (0.010 g, 0.027 mmol) in an atmosphere of nitrogen and sealed in a pressure reactor vessel at 110° C. for 6 h. It was processed as described in the synthesis of Example 129k to obtain the title compound as a white solid. Yield: 0.290 g, (45.95%); 1H NMR (DMSO-d6): δ 1.10-2.00 (m, 1H, cyclohexyl), 2.70 (s, 3H, CH3), 3.20-3.30 (m, 4H, 2CH2), 3.75-3.8 (m, 4H, 2CH2), 3.95 (s, 3H, OCH3), 4.75 (s, 2H, CH2), 6.70 (s, 1H, Ar), 6.90 (s, 1H, Ar), 8.05 (s, 1H, Ar), 8.45 (s, 1H, Ar); MS: m/e (CI+) 519 (M+1).

Workup

  1. customsealed in a pressure reactor vessel at 110° C. for 6 h
  2. customas described in the synthesis of Example 129k

Sources & evidence

ORD record
ord-40d0fc7ad11042e586a67a8f61087a8e
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

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