Methanol → HCID 131728494, compound

HRID 1172524Notes

Reaction equation

HRID 1172524 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH2:7].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]([CH2:6][C:2]5[S:1][CH:5]=[CH:4][CH:3]=5)[CH2:35][CH2:34]4)=[CH:13][C:14]=3[CH2:20][S:19](=[O:22])(=[O:21])[C:18]=2[CH:23]=1)=[O:29]

Participants

4

Reactant 3

HCID 887MethanolHCID 34005(2-Thienylmethyl)amineHCID 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 131728494HCID 131728494, compound

Procedure

Thiophenemethylamine (0.5 g 4.41 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: 0.370 g, (55.38%); 1H NMR (DMSO-d6): δ 2.55-2.60 (m, 4H, 2CH2), 2.70 (s, 3H, CH3), 3.20-3.55 (m, 4H, 2CH2), 3.75 (s, 3H, CH3), 3.95 (s, 3H, OCH3), 4.65 (s, 2H, CH2), 6.75 (s, 1H, Ar), 6.90 (s, 1H, Ar), 6.95-7.05 (m, 2H, Ar), 7.30 (s, 1H, Ar), 8.10 (s, 1H, Ar), 8.40 (s, 1H, Ar); MS: m/e (CI+) 533 (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-86985f3d19de4b04b6fdaec793d45308
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

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