Cyclopropanecarbonyl chloride → HCID 58711982, compound

HRID 2374994Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:11]=[N:12][C:13]([CH:16]([NH:18][C:19]([C:21]3OC=[CH:24][CH:25]=3)=[O:20])[CH3:17])=[CH:14][N:15]=2)=[CH:5][CH:4]=1.NC(C1N=NC(NC2C=CC(OC)=CC=2)=NC=1)C.C1(C(Cl)=O)CC1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]2[N:11]=[N:12][C:13]([CH:16]([NH:18][C:19]([CH:21]3[CH2:25][CH2:24]3)=[O:20])[CH3:17])=[CH:14][N:15]=2)=[CH:7][CH:8]=1

Participants

Reactant 3

HCID 77637Cyclopropanecarbonyl chloride

HCID 58711967HCID 58711967, compound

HCID 587119996-(1-aminoethyl)-N-[4-(methyloxy)phenyl]-1,2,4-triazin-3-amine2×

Product 1

HCID 58711982HCID 58711982, compound

Conditions

Temperature: -78 °C

Procedure

In a similar manner as described for Intermediate 59, using 6-(1-aminoethyl)-N-[4-(methyloxy)phenyl]-1,2,4-triazin-3-amine (Intermediate 47) (100 mg, 0.41 mmol), and cyclopropanecarbonyl chloride (0.043 mL, 0.45 mmol), except the reaction was stirred for 1 h at −78° C., to afford N-[1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]cyclopropanecarboxamide (110 mg) as a yellow solid. 1H NMR (DMSO): δ9.87 (s, 1H), 8.64 (d, J=8.0 HZ, 1H), 8.35 (s, 1H), 7.62 (d, J=8.6 Hz, 2H), 6.91 (d, J=8.6 Hz, 2H), 5.05 (m, 1H), 3.74 (s, 3H), 1.63 (m, 1H), 1.47 (d, J=7.0 Hz, 3H), 0.65 (m, 4H).

Sources & evidence

ORD record: ord-9c74f86ca13742c3bed036e945424a92
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07462614B2

Reaction notes

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