Propyl chloroformate → HCID 67093833, compound

HRID 1661691Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10](C)[C:11]3[C:16]([C:17]=2[C:18]#[N:19])=[CH:15][CH:14]=[C:13]([Cl:20])[CH:12]=3)[CH:6]=[N:7][CH:8]=1.[CH3:22][CH2:23][CH2:24][O:25][C:26](Cl)=[O:27]>>[CH2:24]([O:25][C:26](=[O:27])[NH:1][CH2:2][C:3]1[CH:8]=[N:7][CH:6]=[C:5]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]#[N:19])=[CH:15][CH:14]=[C:13]([Cl:20])[CH:12]=3)[CH:4]=1)[CH2:23][CH3:22]

Participants

Reactant 2

HCID 7998Propyl chloroformate

HCID 58215751HCID 58215751, compound

Product 1

HCID 67093833HCID 67093833, compound

Procedure

2-(5-aminomethyl-pyridin-3-yl)-6-chloro-1-methyl-1H-indole-3-carbonitrile (Example 186e) and N-propyl chloroformate are processed according to the method described in Example 190 to give [5-(6-chloro-3-cyano-1H-indol-2-yl)-pyridin-3-ylmethyl]-carbamic acid propyl ester as a solid. 1H NMR (400 MHz, MeOD) δ ppm 0.98 (t, J=7.3 Hz, 3H), 1.58-1.74 (m, 2H), 3.83 (s, 3H), 4.06 (t, J=6.6 Hz, 2H), 4.49 (s, 2H), 7.38 (dd, J=8.6, 1.77 Hz, 1H), 7.72 (d, J=8.6 Hz, 1H), 7.77 (d, J=1.5 Hz, 1H), 8.09 (t, J=2.0 Hz, 1H), 8.74 (d, J=2.0 Hz, 1H), 8.78 (d, J=2.0 Hz, 1H). HRMS (ESI) m/z 383.1260 [(M+H)+ Calcd for C20H20ClN4O2: 383.1275].

Sources & evidence

ORD record: ord-9beae8d00cbc44f8a8b98e5684a48aea
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030334B2

Reaction notes

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