Dimethylformamide → HCID 135491729, compound

HRID 2108734Notes

Reaction equation

HRID 2108734 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]2[S:14][C:13]([NH2:15])=[N:12][N:11]=2)=[CH:2]1.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH2:24][C:25](O)=[O:26])[CH:21]=[CH:22][CH:23]=1.C(N(CC)CC)C.CN(C=O)C>C1COCC1.[Cl-].[Na+].O.C(OCC)(=O)C.O>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]2[S:14][C:13]([NH:15][C:25](=[O:26])[CH2:24][C:20]3[CH:21]=[CH:22][CH:23]=[C:18]([O:17][CH3:16])[CH:19]=3)=[N:12][N:11]=2)=[CH:2]1

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 15719(3-Methoxyphenyl)acetic acidHCID 136010270HCID 136010270, compound

Product 1

HCID 135491729HCID 135491729, compoundYield 21.5%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A suspension of 5-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1,3,4-thiadiazol-2-amine (0.050 g, 0.23 mmol), 3-methoxyphenylacetic acid (0.038 g, 0.23 mml), triethylamine (0.1 mL) and BtSO2CH3 (0.055 g, 0.28 mml) in THF (3 mL) and DMF (0.3 mL) was heated in a microwave oven for 20 min. The brown solution was added to water (50 mL) and ethyl acetate (50 mL). Brine (10 ml) was added to separate the layers. The organic phase was separated and washed with water (2×50 mL). The organic layer was concentrated to give a solid which was placed in a small Buchner funnel and washed with methanol (2×5 mL) and ethyl acetate (2×5 mL). The brown solid collected was dried under vacuum to afford the desired product (0.018 g, 21%).

Workup

  1. customto separate the layers
  2. customThe organic phase was separated
  3. washwashed with water (2×50 mL)
  4. concentrationThe organic layer was concentrated
  5. customto give a solid which
  6. washwashed with methanol (2×5 mL) and ethyl acetate (2×5 mL)
  7. customThe brown solid collected
  8. customwas dried under vacuum

Sources & evidence

ORD record
ord-ba890854a2334c299052a0baa095e85d
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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