Hydrochloric Acid → HCID 89497862, compound

HRID 1778907Notes

Reaction equation

HRID 1778907 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[N:28]=[C:27]([C:29]([OH:31])=O)[C:26]([C:32]3[CH:33]=[N:34][N:35]([CH2:38][C:39]4([O:47][CH3:48])[CH2:44][CH2:43][CH2:42][C:41]([CH3:46])([CH3:45])[CH2:40]4)[C:36]=3[CH3:37])=[CH:25][CH:24]=1)[CH2:19][CH2:18]2)=[O:12].[CH3:49][S:50]([NH2:53])(=[O:52])=[O:51].Cl.C(N=C=NCCCN(C)C)C.Cl>CN(C)C1C=CN=CC=1.ClCCl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[CH:24]=[CH:25][C:26]([C:32]3[CH:33]=[N:34][N:35]([CH2:38][C:39]4([O:47][CH3:48])[CH2:44][CH2:43][CH2:42][C:41]([CH3:45])([CH3:46])[CH2:40]4)[C:36]=3[CH3:37])=[C:27]([C:29](=[O:31])[NH:53][S:50]([CH3:49])(=[O:52])=[O:51])[N:28]=1)[CH2:19][CH2:18]2)=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 89498248HCID 89498248, compound

Product 1

HCID 89497862HCID 89497862, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of EXAMPLE 157E (0.051 g), methanesulfonamide (0.015 g), 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride.HCl (0.037 g) and 4-dimethylaminopyridine (0.019 g) were stirred together in dichloromethane (1 mL) at room temperature overnight. The reaction mixture was loaded onto silica gel and eluted using a gradient of 0.5% to 3.25% methanol/dichloromethane to provide the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ ppm 12.84 (s, 1H), 11.81 (s, 1H), 8.03 (d, 1H), 7.79 (d, 1H), 7.62 (d, 1H), 7.56-7.41 (m, 3H), 7.41-7.32 (m, 2H), 7.29 (s, 1H), 7.00 (d, 1H), 4.96 (s, 2H), 4.00 (d, 2H), 3.93 (t, 2H), 3.16 (s, 3H), 3.11 (s, 3H), 3.03 (t, 2H), 2.13 (s, 3H), 1.71 (d, 1H), 1.58-1.00 (m, 7H), 0.96 (s, 3H), 0.84 (s, 3H).

Workup

  1. washeluted

Sources & evidence

ORD record
ord-84960a9850f544b3b4c5ee7ef5be3906
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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