N-Methylpropylamine → 1-(2-Amino-5-(thiophen-2-yl)phenyl)-3-cyclopropylurea

HRID 2201696Notes

Reaction equation

[CH3:1][NH:2][CH2:3][CH2:4][CH3:5].C1(N)CC1.C1(C2C=CC([N+]([O-])=[O:23])=C(C=2)N)CCCC=1.[N+:25]([C:28]1[CH:34]=[CH:33][C:32]([C:35]2[S:36][CH:37]=[CH:38][CH:39]=2)=[CH:31][C:29]=1[NH2:30])([O-])=O>>[NH2:25][C:28]1[CH:34]=[CH:33][C:32]([C:35]2[S:36][CH:37]=[CH:38][CH:39]=2)=[CH:31][C:29]=1[NH:30][C:1]([NH:2][CH:3]1[CH2:5][CH2:4]1)=[O:23]

Participants

Reactant 4

HCID 12315N-Methylpropylamine

HCID 69828Cyclopropylamine

HCID 236564282-Nitro-5-(thiophen-2-yl)aniline

HCID 867125235-(Cyclopent-1-en-1-yl)-2-nitroaniline

Product 1

HCID 867125281-(2-Amino-5-(thiophen-2-yl)phenyl)-3-cyclopropylurea

Procedure

1-(2-amino-5-(thiophen-2-yl)phenyl)-3-cyclopropylurea (100) was prepared by substituting N-methylpropan-1-amine in Scheme 25 with cyclopropanamine and by substituting 5-(cyclopent-1-en-1-yl)-2-nitroaniline in Scheme 25 with 2-nitro-5-(thiophen-2-yl)aniline. ESI+ MS: m/z 273 ([M]+), 1H NMR (500 MHz, d6-DMSO): δ 7.62 (d, J=2.0 Hz, 1H), 7.50 (s, 1H), 7.33 (d, J=4.5 Hz, 1H), 7.18 (d, J=3.0 Hz, 1H), 7.11 (dd, J=2.0, 8.0 Hz, 1H), 7.03 (dd, J=3.5, 4.5 Hz, 1H), 6.72 (d, J=8.5 Hz, 1H), 6.47 (s, 1H), 4.90 (s, 2H), 2.58-2.50 (m, 1H), 0.65-0.61 (m, 2H), 0.45-0.40 (m, 2H).

Sources & evidence

ORD record: ord-e45a615f29064a51ab40f11f44f3dbfe
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365498B2

Reaction notes

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