Hydrochloric Acid → HCID 131730336, compound

HRID 1948329Notes

Reaction equation

HRID 1948329 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:19]=[C:20]([C:26]([C:29]([NH:31]C(C)(C3C=CC=CC=3)C)=[O:30])=[CH:27][N:28]=2)[C:21]([O:23]CC)=[O:22])[CH2:14][C@H:13]1[O:41][CH3:42])=[O:10].Cl>CO.O>[NH2:31][C:29]([C:26]1[C:20]([C:21]([OH:23])=[O:22])=[CH:19][C:18]([N:15]2[CH2:16][CH2:17][C@H:12]([NH:11][C:9]([C:3]3[NH:4][C:5]([CH3:8])=[C:6]([Cl:7])[C:2]=3[Cl:1])=[O:10])[C@H:13]([O:41][CH3:42])[CH2:14]2)=[N:28][CH:27]=1)=[O:30]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131730329HCID 131730329, compound

Product 1

HCID 131730336HCID 131730336, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 85 mg (0.17 mmol) of Cis(±)-ethyl 5-(aminocarbonyl)-2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)isonicotinate (Example 198) and 86 mg (0.50 mmol) Ba(OH)2 in 3 ml MeOH and 2 ml water was heated at 120° C. for 1 h. The mixture was acidified to about pH=4 with 1N HCl and extracted 4 times with EtOAc. The EtOAc was concentrated and the residue was purified by reverse phase HPLC (20-40% CH3CN gradient in water with 0.1% TFA) to afford 8 mg of product as a white solid. MS (ES) MH+: 470 for C19H21Cl2N5O5; NMR: 1.5-1.8, (m, 3H), 2.2 (s, 3H), 3.0-3.2 (m, 2H), 3.3 (s, 3H), 3.5 (m, 2H), 4.2-4.5 (m, 2H), 4.9 (d, 1H), 6.9 (s, 1H), 7.1-7.3 (m, 2H), 7.8 (s, 1H), 8.4 (s, 1H), 12.1 (s, 1H), 13.1 (s, 1H).

Workup

  1. extractionextracted 4 times with EtOAc
  2. concentrationThe EtOAc was concentrated
  3. customthe residue was purified by reverse phase HPLC (20-40% CH3CN gradient in water with 0.1% TFA)

Sources & evidence

ORD record
ord-3a1c48e9406b47588c348f3ffa8e066f
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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