Hydrochloric Acid → HCID 118037213, compound

HRID 1508982Notes

Reaction equation

HRID 1508982 reaction equation
[NH2:1][C:2](=[O:33])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[CH:16]=[C:15]([N:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]3)[N:14]=[C:13]3[CH2:30][CH2:31][CH2:32][C:12]=23)=[CH:6][CH:5]=1.[ClH:34]>CO>[ClH:34].[N:17]1([C:15]2[N:14]=[C:13]3[CH2:30][CH2:31][CH2:32][C:12]3=[C:11]([NH:10][C:7]3[CH:8]=[CH:9][C:4]([CH2:3][C:2]([NH2:1])=[O:33])=[CH:5][CH:6]=3)[CH:16]=2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90338578HCID 90338578, compound

Product 1

HCID 118037213HCID 118037213, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of tert-butyl 4-(4-((4-(2-amino-2-oxoethyl)phenyl)amino)-6,7-dihydro-5H-cyclopenta[b]pyridin-2-yl)piperazine-1-carboxylate in methanol (3 mL) was added HCl (6 M, 0.1 mL). The mixture was heated to 65° C. for 16 h. The Boc group was removed, however, the amide function was replaced with a methyl ester group. The mixture was concentrated and following general procedure C, desired product was obtained after forming the hydrochloride salt (0.015 g, 50%) as an orange-brown solid. MW=424.37. 1H NMR (DMSO-d6, 500 MHz) δ 13.26 (s, 1H), 9.40-9.28 (m, 3H), 7.53 (s, 1H), 7.34 (d, J=8.5 Hz, 2H), 7.29 (d, J=8.5 Hz, 2H), 6.91 (s, 1H), 6.07 (s, 1H), 3.64-3.57 (m, 4H), 3.41 (s, 2H), 3.20 (br s, 4H), 3.02 (t, J=7.5 Hz, 2H), 2.78 (t, J=7.5 Hz, 2H), 2.15 (quin, J=7.5 Hz, 2H); APCI MS m/z, 352 [M+H]+.

Workup

  1. customThe Boc group was removed
  2. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-113063fc67ce4864b9fb8e22a8cc6758
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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