Triethylamine → HCID 11989753, compound

HRID 1715268Notes

Reaction equation

HRID 1715268 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[N:12]=[C:13]([C:16](Cl)=[O:17])[S:14][CH:15]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].[OH:19][CH2:20][CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(N(CC)CC)C>C1COCC1.C(Cl)Cl>[OH:19][CH2:20][CH:21]1[CH2:26][CH2:25][N:24]([C:16]([C:13]2[S:14][CH:15]=[C:11]([C:7]3[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][C:8]=3[CH3:10])[N:12]=2)=[O:17])[CH2:23][CH2:22]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 4207714-PiperidinemethanolHCID 86621993HCID 86621993, compound

Product 1

HCID 11989753HCID 11989753, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2′-Acetylamino-4′-methyl-[4,5′]bithiazolyl-2-carbonyl chloride, prepared as in Step I of Example 13, described above, (200 mg, 0.66 mmol, 1 eq.), is dissolved in THF (8 ml) and DCM (4 ml). 4-(Hydroxymethyl)piperidine (Maybridge)(76.3 mg; 0.66 mmol; 1 eq.) and triethylamine (0.19 ml; 1.33 mmol; 2 eq.) are added and the mixture is stirred overnight at rt. Solvents are evaporated and the crude product is crystallized in MeOH, affording Compound (27) as a brown solid (106.3 mg; 42%). 1H NMR (DMSO-d6, 300 MHz) δ 1.05-1.30 (m, 2H), 1.65-1.87 (m, 3H), 2.14 (s, 3H), 2.50 (s, 3H), 2.86 (m, 1H), 3.20 (m, 1H), 3.28 (m, 2H), 4.48 (m, 1H), 4.52 (t, J=4.5 Hz, 1H), 5.16 (m, 1H), 7.97 (s, 1H), 12.16 (s, 1H). M− (ESI): 379.20; M+ (ESI): 381.19. HPLC (method A), Rt: 2.47 min (purity: 99%).

Workup

  1. customSolvents are evaporated
  2. customthe crude product is crystallized in MeOH

Sources & evidence

ORD record
ord-323f156954ec4225a0a9d9265cc5a908
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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