4-(Pyrrolidin-1-yl)benzylamine → N-(3-methyl-5-isoquinolinyl)-N'-[4-(1-pyrrolidinyl)benzyl]urea

HRID 887255Notes

Reaction equation

HRID 887255 reaction equation
[N:1]1([C:6]2[CH:13]=[CH:12][C:9]([CH2:10][NH2:11])=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[N:14]([C:17]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[CH:19]=[C:20]([CH3:27])[N:21]=[CH:22]2)=[C:15]=[O:16].N(C1C=CC=C2C=1C=CN=C2)=C=O>>[CH3:27][C:20]1[N:21]=[CH:22][C:23]2[C:18]([CH:19]=1)=[C:17]([NH:14][C:15]([NH:11][CH2:10][C:9]1[CH:12]=[CH:13][C:6]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:7][CH:8]=1)=[O:16])[CH:26]=[CH:25][CH:24]=2

Participants

4

Reactant 3

HCID 70178344-(Pyrrolidin-1-yl)benzylamineHCID 115863575-IsocyanatoisoquinolineHCID 222283825-Isocyanato-3-methylisoquinoline

Product 1

HCID 10361181N-(3-methyl-5-isoquinolinyl)-N'-[4-(1-pyrrolidinyl)benzyl]urea

Procedure

The title compound was prepared using the procedure described in Example 61B using 4-(1-pyrrolidinyl)benzylamine and the product from Example 154A instead of 4-cyanobenzyl alcohol and the product from Example 61A. 1H NMR (300 MHz, DMSO-d6) δ 9.15 (s, 1H), 8.54 (s, 1H), 8.27 (d, 1H, J=7.5 Hz), 7.73 (s, 1H), 7.67 (d, 1H, J=7.5 Hz), 7.49 (t, 1H, J=7.5 Hz), 7.16 (d, 2H, J=9 Hz), 6.84 (t, 1H, J=6 Hz), 6.53 (d, 2H, J=9 Hz), 4.22 (d, 2H, J=6 Hz), 3.20 (m, 4H), 2.63 (s, 3H), 1.94 (m, 4H); MS (ESI) 361 (M+H)+. Anal. Calcd for C22H24N4O.0.2H2O: C, 72.58; H, 6.76; N, 15.39. Found: C, 72.33; H, 6.64; N, 15.22.

Sources & evidence

ORD record
ord-846e99bbbac74c6785721ec98527226d
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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