Dimethylformamide → Ammonium Chloride

HRID 1530032Notes

Reaction equation

HRID 1530032 reaction equation
[Cl:1]C1C=CC=C[C:3]=1[C:8]1[N:9]=C([C:16]2[C:17](C)=[N:18][N:19]3C=CC=[CH:21][C:20]=23)SC=1C(O)=O.[CH2:26]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])C.C[N:34]([CH3:37])[CH:35]=[O:36]>>[Cl-:1].[NH4+:9].[OH:36][N:28]1[C:31]2[CH:32]=[CH:21][CH:20]=[CH:16][C:17]=2[N:18]=[N:19]1.[ClH:1].[CH3:31][N:28]([CH3:26])[CH2:29][CH2:30][CH2:37][N:34]=[C:35]=[N:9][CH2:8][CH3:3]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 66855390HCID 66855390, compound

Product 3

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Procedure

Using 4-(2-chlorophenyl)-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxylic acid (350 mg, 0.94 mmol) produced in the above, ammonium chloride (3.0 g, 56 mmol), triethylamine (4.5 mL), 1-hydroxybenzotriazole (70 mg, 0.52 mmol), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (2.0 g, 10 mmol) and N,N-dimethylformamide (50 mL) as starting materials and in the same manner as in Example 13-B(v), the title compound (341 mg, 97%) was obtained as a yellow solid.

Sources & evidence

ORD record
ord-65beee8459484a229f2c8d1016f9fa8b
Source dataset
uspto-grants-2015_07
Patent number
US09090601B2

Reaction notes

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