1-(Pyridazin-3-yl)methanamine → HCID 57919821, compound

HRID 1882463Notes

Reaction equation

HRID 1882463 reaction equation
FC1C=C(CN)C=NC=1.[N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][NH2:17])[N:11]=1.[CH:18]1([CH2:21][N:22]2[CH2:26][CH2:25][N:24]([C:27]3[S:28][C:29]([C:33](O)=[O:34])=[C:30]([CH3:32])[N:31]=3)[C:23]2=[O:36])[CH2:20][CH2:19]1>>[CH:18]1([CH2:21][N:22]2[CH2:26][CH2:25][N:24]([C:27]3[S:28][C:29]([C:33]([NH:17][CH2:16][C:12]4[N:11]=[N:10][CH:15]=[CH:14][CH:13]=4)=[O:34])=[C:30]([CH3:32])[N:31]=3)[C:23]2=[O:36])[CH2:19][CH2:20]1

Participants

4

Reactant 3

HCID 226395181-(Pyridazin-3-yl)methanamineHCID 45116207(5-Fluoropyridin-3-yl)methanamineHCID 579198202-(3-(Cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 57919821HCID 57919821, compoundYield 17%

Procedure

Following the procedure as describe in Example 12, making variations as required to replace (5-fluoropyridin-3-yl)methanamine with pyridazin-3-ylmethanamine to react with 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a colorless solid in 17% yield: mp 187-189° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 9.11 (d, J=4.2 Hz, 1H), 7.59-7.56 (m, 1H), 7.49-7.45 (m, 1H), 7.03-7.00 (m, 1H), 4.88 (d, J=5.4 Hz, 2H), 4.14-4.09 (m, 2H), 3.73-3.67 (m, 2H), 3.19 (d, J=7.1 Hz, 2H), 2.62 (s, 3H), 0.97-0.92 (m, 1H), 0.60-0.54 (m, 2H), 0.27-0.22 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 163.0, 159.4, 158.1, 155.2, 152.8, 150.7, 126.9, 126.2, 117.4, 48.6, 43.7, 42.2, 42.1, 17.4, 8.9, 3.4; MS (ES+) m/z 373.2 (M+1).

Sources & evidence

ORD record
ord-62fe5c47dc6946ebbee3f07f5dc28aee
Source dataset
uspto-grants-2012_11
Patent number
US08318949B2

Reaction notes

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