Hydrochloric Acid → HCID 178458564, compound

HRID 478602Notes

Reaction equation

HRID 478602 reaction equation
Cl[C:2]1[C:11]2[C:10](=[O:12])[N:9]=[C:8]([C:13]3[CH:14]=[C:15]([S:23]([N:26]4[CH2:30][CH2:29][C@@H:28]([N:31]([CH3:33])[CH3:32])[CH2:27]4)(=[O:25])=[O:24])[CH:16]=[CH:17][C:18]=3[O:19][CH2:20][CH2:21][CH3:22])[NH:7][C:6]=2[C:5]2=[CH:34][N:35]([CH2:37][C:38]3[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=3)[N:36]=[C:4]2[N:3]=1.[Cl:46][C:47]1[CH:48]=[C:49]([CH:52]=[CH:53][C:54]=1[O:55][CH3:56])[CH2:50][NH2:51].Cl.CCN(C(C)C)C(C)C>CCCCO>[CH3:32][N:31]([CH3:33])[C@@H:28]1[CH2:29][CH2:30][N:26]([S:23]([C:15]2[CH:16]=[CH:17][C:18]([O:19][CH2:20][CH2:21][CH3:22])=[C:13]([C:8]3[NH:7][C:6]4[C:5]5[C:4](=[N:36][N:35]([CH2:37][C:38]6[CH:39]=[CH:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=6)[CH:34]=5)[N:3]=[C:2]([NH:51][CH2:50][C:49]5[CH:52]=[CH:53][C:54]([O:55][CH3:56])=[C:47]([Cl:46])[CH:48]=5)[C:11]=4[C:10](=[O:12])[N:9]=3)[CH:14]=2)(=[O:25])=[O:24])[CH2:27]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 7380383-Chloro-4-methoxybenzylamineHCID 178458563HCID 178458563, compound

Product 1

HCID 178458564HCID 178458564, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of (3R)-1-[[3-(5-Chloro-4,8-dihydro-8-[(4-methoxyphenyl)methyl]-4-oxo-1H-pyrazolo[4′,3′:5,6]pyrido[4,3-d]pyrimidin-2-yl)-4-propoxyphenyl]sulfonyl]-3-(dimethylamino)pyrrolidine (39 mg, 0.06 mmol), 3-chloro-4-methoxybenzylamine.HCl (25 mg, 0.12 mmol) and DIEA (78 mg, 0.6 mmol) in n-BuOH was heated at 125° C. under nitrogen for 4 h. The reaction mixture was concentrated and the residue was chromatographed (silica gel, 5% MeOH in DCM) to give the desired product (42.6 mg) as a yellow solid. LC: 4.36′ (Gradient 1); MH+: 787.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was chromatographed (silica gel, 5% MeOH in DCM)

Sources & evidence

ORD record
ord-c2c7ae3f99964b8d982be8059bd51749
Source dataset
uspto-grants-2003_11
Patent number
US06642244B2

Reaction notes

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