Hydrochloric Acid → HCID 46841322, compound

HRID 1896596Notes

Reaction equation

HRID 1896596 reaction equation
[Li+].[OH-].[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[NH:12][C:13]([N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:25]3[N:30]=[C:29]([C:31]([O:33]C)=[O:32])[C:28]([O:35][CH2:36][CH2:37][CH2:38][O:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[CH:27][CH:26]=3)[CH:23]=2)[N:18]([CH3:46])[CH2:17][CH2:16]1)=[O:14].Cl>CO.O>[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[NH:12][C:13]([N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:25]3[N:30]=[C:29]([C:31]([OH:33])=[O:32])[C:28]([O:35][CH2:36][CH2:37][CH2:38][O:39][C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)=[CH:27][CH:26]=3)[CH:23]=2)[N:18]([CH3:46])[CH2:17][CH2:16]1)=[O:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59418729HCID 59418729, compound

Product 1

HCID 46841322HCID 46841322, compoundYield 61.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

The title compound 6-(4-(benzo[d]thiazol-2-ylcarbamoyl)-1-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)-3-(3-phenoxypropoxy)picolinic acid (26) was prepared by the following procedure: LiOH (12 mg, 10 eq) was added to a mixture of Methyl 6-(4-(benzo[d]thiazol-2-ylcarbamoyl)-1-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)-3-(3-phenoxypropoxy)picolinate (26E) (25 mg, 0.041 mmol) in MeOH (0.5 mL) and water (0.25 mL) at rt. The mixture was heated to 55° C. for 14 hours, cooled to 0° C. and acidified with 1N HCl to pH˜4. The resulting precipitate was filtered, washed with water and dried in vacuo to provide 15 mg (61%) of the desired product 6-(4-(benzo[d]thiazol-2-ylcarbamoyl)-1-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)-3-(3-phenoxypropoxy)picolinic acid (26): 1H NMR (300 MHz, DMSO-d6) δ 8.13 (1H, bs), 7.83 (1H, d), 7.80 (1H, d), 7.65 (2H, m), 7.37 (1H, t), 7.32-7.18 (4H, m), 6.94 (3H, m), 6.79 (1H, d), 4.26 (2H, t), 4.15 (2H, t), 4.02 (2H, t), 3.41 (2H, t), 2.97 (3H, s), 2.17 (2H, t). MS (ESI(+)): m/z 596.1 (M+H).

Workup

  1. customThe title compound 6-(4-(benzo[d]thiazol-2-ylcarbamoyl)-1-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)-3-(3-phenoxypropoxy)picolinic acid (26) was prepared by the following procedure
  2. temperaturecooled to 0° C.
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-83baa82eb83a445891cbede4e2960645
Source dataset
uspto-grants-2013_08
Patent number
US08518970B2

Reaction notes

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