3-Phenylpropylamine → N-{6-[(cyclopentylmethyl)carbamoyl]pyridazin-3-yl}-1,3-dihydro-2H-isoindole-2-carboxamide

HRID 624210Notes

Reaction equation

HRID 624210 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][NH2:10])[CH:6]=[CH:5]C=CC=1.[CH2:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][N:12]1[C:20]([NH:22][C:23]1[N:28]=[N:27][C:26]([C:29]([OH:31])=O)=[CH:25][CH:24]=1)=[O:21].C1C2C(=CC=CC=2)CN1C(NC1C=CC(C(O)=O)=CC=1)=O>>[CH:8]1([CH2:9][NH:10][C:29]([C:26]2[N:27]=[N:28][C:23]([NH:22][C:20]([N:12]3[CH2:11][C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH2:13]3)=[O:21])=[CH:24][CH:25]=2)=[O:31])[CH2:5][CH2:6][CH2:1][CH2:7]1

Participants

4

Reactant 3

HCID 162593-PhenylpropylamineHCID 62230337HCID 62230337, compoundHCID 687492076-(Isoindoline-2-carboxamido)pyridazine-3-carboxylic acid

Product 1

HCID 57510217N-{6-[(cyclopentylmethyl)carbamoyl]pyridazin-3-yl}-1,3-dihydro-2H-isoindole-2-carboxamide

Procedure

The title compound was prepared as described in Example 1C, substituting cyclopentylmethamine for 3-phenylpropan-1-amine and 6-(isoindoline-2-carboxamido)pyridazine-3-carboxylic acid for 4-(isoindoline-2-carboxamido)benzoic acid. 1H NMR (300 MHz, DMSO-d6) δ 9.97 (s, 1H), 9.00 (t, J=6.1 Hz, 1H), 8.31 (d, J=9.3 Hz, 1H), 8.11 (d, J=9.3 Hz, 1H), 7.41-7.28 (m, 4H), 5.13-4.72 (m, 4H), 3.31-3.16 (m, 2H), 2.22 (p, J=7.3 Hz, 1H), 1.70-1.45 (m, 6H), 1.38-1.20 (m, 2H); MS (ESI(+)) m/e 366 (M+H)+.

Sources & evidence

ORD record
ord-995f0fd5d99b454da61668a031879491
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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