Propionyl chloride → HCID 18368020, compound

HRID 379882Notes

Reaction equation

[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[N:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:3]=1[C:17]([C:19]1[CH:24]=[C:23]([N:25]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:22]=[CH:21][N:20]=1)=[O:18].[C:40](Cl)(=[O:43])[CH2:41][CH3:42]>>[C:29]([O:28][C:26]([N:25]([C:23]1[CH:22]=[CH:21][N:20]=[C:19]([C:17]([C:3]2[N:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:5]3[C:10]([C:2]=2[NH:1][C:40](=[O:43])[CH2:41][CH3:42])=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=3)=[O:18])[CH:24]=1)[C:33]([O:35][C:36]([CH3:38])([CH3:37])[CH3:39])=[O:34])=[O:27])([CH3:30])([CH3:31])[CH3:32]

Participants

Reactant 2

HCID 62324Propionyl chloride

HCID 18368030HCID 18368030, compound

Product 1

HCID 18368020HCID 18368020, compound

Procedure

The title compound was prepared according ot the procedure described in step 1 of Example 2 (Method A) employing 3-amino-2-[4-[N,N-bis(tert-butoxycarbonyl)amino]pyridine-2-carbonyl]-6-chloro-1-(ethoxycarbonyl)indole (step 2) and propionyl chloride. 1H-NMR (CDCl3) δ: 9.52 (1 H, br s), 8.61 (1 H, d, J=5.1 Hz), 8.21 (1 H, d, J=1.8 Hz), 8.05 (1 H, d, J=8.7 Hz), 7.95 (1 H, d, J=2.1 Hz), 7.28-7.23 (2 H, m), 3.93 (2 H, q, J=7.1 Hz), 2.51 (2 H, q, J=7.4 Hz), 1.50 (18 H, s), 1.26 (3 H, t, J=7.4 Hz), 1.02 (3 H, t, J=7.1 Hz).

Sources & evidence

ORD record: ord-055f62067d3646d78b520b4984e10c82
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06300363B1

Reaction notes

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