Hydrochloric Acid → HCID 21945984, compound

HRID 1295760Notes

Reaction equation

HRID 1295760 reaction equation
[O:1]=[C:2]1[CH:10]([C:11]2[C:16]3=[C:17]([CH3:23])[C:18]([C:20](O)=[O:21])=[CH:19][N:15]3[N:14]=[CH:13][N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[NH2:57][CH2:58][CH2:59][CH2:60][N:61]1[CH2:65][CH2:64][CH2:63][CH2:62]1.Cl>CN(C=O)C.ClCCl>[O:1]=[C:2]1[CH:10]([C:11]2[C:16]3=[C:17]([CH3:23])[C:18]([C:20]([NH:57][CH2:58][CH2:59][CH2:60][N:61]4[CH2:65][CH2:64][CH2:63][CH2:62]4)=[O:21])=[CH:19][N:15]3[N:14]=[CH:13][N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 316701-PyrrolidinepropanamineHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 21945946HCID 21945946, compound

Product 1

HCID 21945984HCID 21945984, compoundYield 37.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 95 (50 mg, 0.16 mmol) in DMF (1 mL), dichloromethane (0.5 mL) were added PyBrop (113 mg, 0.24 mmol) and diisopropylethyl amine (0.08 mL, 0.5 mL). After 10 min, 1-(3-aminopropyl)pyrrolidine (61 mg, 0.48 mmol) was added. After 15 h, the reaction mixture was purified by preparative RP HPLC. The yellow oil obtained was converted to the HCl salt and lyophilized to afford a red orange solid (25 mg, 34%). MS: (M+H)+=419.

Workup

  1. waitAfter 15 h
  2. customthe reaction mixture was purified by preparative RP HPLC
  3. customThe yellow oil obtained

Sources & evidence

ORD record
ord-711522574958453283eebb0172e11e15
Source dataset
uspto-grants-2007_07
Patent number
US07244733B2

Reaction notes

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