Methanol → HCID 131728495, compound

HRID 1172525Notes

Reaction equation

HRID 1172525 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].Cl[CH2:12][CH2:13][N:14]([CH2:37][CH2:38]Cl)[C:15]1[CH:35]=[C:34]([Cl:36])[C:18]2[O:19][C:20]3[C:29]([CH3:30])=[CH:28][C:27]([C:31]([OH:33])=[O:32])=[CH:26][C:21]=3[S:22](=[O:25])(=[O:24])[CH2:23][C:17]=2[CH:16]=1.[CH3:40]O>>[CH3:40][O:33][C:31]([C:27]1[CH:28]=[C:29]([CH3:30])[C:20]2[O:19][C:18]3[C:34]([Cl:36])=[CH:35][C:15]([N:14]4[CH2:13][CH2:12][N:6]([CH2:5][C:4]5[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=5[O:2][CH3:1])[CH2:38][CH2:37]4)=[CH:16][C:17]=3[CH2:23][S:22](=[O:25])(=[O:24])[C:21]=2[CH:26]=1)=[O:32]

Participants

4

Reactant 3

HCID 887MethanolHCID 812922-MethoxybenzylamineHCID 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 131728495HCID 131728495, compound

Procedure

2-Methoxybenzylamine (1 mL, 2.28 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, 0.02 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: 0.250 g, (35.81%); 1H NMR (DMSO-d6): δ 2.60-2.70 (m, 4H, 2CH2), 2.72 (s, 3H, CH3), 3.20-3.30 (m, 4H, 2CH2), 3.70 (s, 2H, CH2), 3.90 (s, 3H, OCH3), 3.95 (s, 3H, CH3), 4.70 (s, 2H, CH2), 6.80 (s, 1H, Ar), 6.90 (s, 1H, Ar), 6.95-7.00 (m, 2H, Ar), 7.30 (t, 1H, Ar), 7.40 (d, 1H, Ar), 8.10 (s, 1H, Ar), 8.50 (s, 1H, Ar); MS: m/e (CI+) 557 (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-814ca3ee35c342e58715aec564115391
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

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