Pyridine → HCID 10258773, compound

HRID 2108348Notes

Reaction equation

HRID 2108348 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2([C:25]([NH:27][CH2:28][C:29]3[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[C:31]([C:39]([F:42])([F:41])[F:40])[CH:30]=3)=[O:26])[CH2:11][CH2:10][CH:9]([N:12]3[CH2:17][CH2:16][CH:15]([C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)[CH2:14][CH2:13]3)[CH2:8]2)[N:6]=1.[C:43](OC(=O)C)(=[O:45])[CH3:44].N1C=CC=CC=1>C(Cl)Cl>[C:43]([NH:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2([C:25]([NH:27][CH2:28][C:29]3[CH:34]=[C:33]([C:35]([F:36])([F:37])[F:38])[CH:32]=[C:31]([C:39]([F:42])([F:41])[F:40])[CH:30]=3)=[O:26])[CH2:11][CH2:10][CH:9]([N:12]3[CH2:13][CH2:14][CH:15]([C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)[CH2:16][CH2:17]3)[CH2:8]2)[N:6]=1)(=[O:45])[CH3:44]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 10416351HCID 10416351, compound

Product 1

HCID 10258773HCID 10258773, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.040 g of the compound from EXAMPLE 44, 0.20 g of acetic anhydride and 0.40 g of pyridine in 1.0 mL of CH2Cl2 was stirred overnight, evaporated and dried in vacuo. The residue was purified by preparative TLC (10% [aq. NH4OH/MeOH 1/9]/CH2Cl2). The title compound (0.037 g) was obtained as a white solid. 1H NMR (400 MHz, CDCl3): δ 1.60-2.24 (m, 9H), 2.27(s, 3H), 2.50 (m, 4H), 2.85 (m, 1H), 3.20 (m, 2H), 4.55 (m, 2H), 6.83 (s, 1H), 6.97-7.20 (m,5H), 7.64 (s,2H), 7.76 (s, 1H), 9.06 (broad, 1H). LC-MS: m/z 657 (M+1).

Workup

  1. customevaporated
  2. customdried in vacuo
  3. customThe residue was purified by preparative TLC (10% [aq. NH4OH/MeOH 1/9]/CH2Cl2)

Sources & evidence

ORD record
ord-6f7b373632af4c4caeba6114eec84a5e
Source dataset
uspto-grants-2009_04
Patent number
US07514431B2

Reaction notes

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