4-Pyridinemethanamine → HCID 57619347, compound

HRID 1024225Notes

Reaction equation

HRID 1024225 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.Cl[C:19]1[S:20][C:21]([CH:25]=[O:26])=[C:22]([Cl:24])[N:23]=1>O1CCCC1>[Cl:24][C:22]1[N:23]=[C:19]([NH:1][CH2:2][C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)[S:20][C:21]=1[CH:25]=[O:26]

Participants

5

Reactant 3

HCID 773174-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 14886722,4-Dichloro-1,3-thiazole-5-carboxaldehyde

Product 1

HCID 57619347HCID 57619347, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-(aminomethyl)pyridine (516, 1.16 mL, 11.5 mmol) and N,N-diisopropylethylamine (3.8 mL, 22 mmol) in tetrahydrofuran (50 mL) was added 2,4-dichloro-thiazole-5-carbaldehyde (93, 2.0 g, 11.0 mmol) in tetrahydrofuran (5 mL) at room temperature. The reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into ice water, extracted with ethyl acetate, washed with brine, and dried over sodium sulfate. The crude compound 4-chloro-2-[(pyridin-4-ylmethyl)-amino]-thiazole-5-carbaldehyde (517) was used for the next step without purification.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe crude compound 4-chloro-2-[(pyridin-4-ylmethyl)-amino]-thiazole-5-carbaldehyde (517) was used for the next step without purification

Sources & evidence

ORD record
ord-46cef325238c4f88b4496b9f1d4cff9e
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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