3-Aminopropionitrile → HCID 46833856, compound

HRID 1882168Notes

Reaction equation

HRID 1882168 reaction equation
[F:1][CH:2]([F:29])[O:3][C:4]1[C:5]([O:23][CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[C:6](/[CH:10]=[CH:11]/[C:12]2[N:13]=[C:14]3[N:18]([C:19]=2[C:20](O)=[O:21])[CH:17]=[CH:16][S:15]3)[CH:7]=[CH:8][CH:9]=1.[NH2:30][CH2:31][CH2:32][C:33]#[N:34].CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.C1COCC1.CN(C=O)C>[C:31]([CH2:32][CH2:33][NH:34][C:20]([C:19]1[N:18]2[C:14]([S:15][CH:16]=[CH:17]2)=[N:13][C:12]=1/[CH:11]=[CH:10]/[C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH:2]([F:1])[F:29])[C:5]=1[O:23][CH2:24][C:25]([CH3:27])([CH3:28])[CH3:26])=[O:21])#[N:30]

Participants

7

Reactant 3

HCID 16473-AminopropionitrileHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 684073456-{(E)-2-[3-(Difluoromethoxy)-2-(2,2-dimethylpropoxy)phenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylic acid

Product 1

HCID 46833856HCID 46833856, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to the general procedure (Method B) by coupling Intermediate 7A (80 mg, 0.189 mmol) with 3-aminopropanenitrile (14.56 mg, 0.208 mmol) in the presence of EDCI hydrochloride (72 mg, 0.378 mmol), DMAP (21 mg, 0.189 mmol) in a mixture of THF and DMF (1:1, 4 mL) to give 60 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.08 (s, 9H), 2.82-2.86 (m, 2H), 3.52-3.60 (m, 4H), 7.16 (t, J=73.5 Hz, 1H), 7.18-7.30 (m, 2H), 7.37-7.52 (m, 2H), 7.72-7.88 (m, 2H), 8.00-8.06 (m, 1H), 8.59 (br s, 1H); APCI-MS (m/z) 475.28 (MH)+.

Sources & evidence

ORD record
ord-3c3818e74c58401a84103614684bf0ae
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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