Methyl chloroformate → 4-{4-Methoxy-2-[(morpholine-4-carbonyl)-amino]-benzothiazol-7-yl}-piperidine-1-carboxylic acid methyl ester

HRID 1582153Notes

Reaction equation

HRID 1582153 reaction equation
Cl.[CH3:2][O:3][C:4]1[C:9]2[N:10]=[C:11]([NH:13][C:14]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[O:15])[S:12][C:8]=2[C:7]([CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH3:35][O:36][C:37](Cl)=[O:38].C(=O)(O)[O-].[Na+]>C1COCC1.O>[CH3:35][O:36][C:37]([N:25]1[CH2:26][CH2:27][CH:22]([C:7]2[C:8]3[S:12][C:11]([NH:13][C:14]([N:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)=[O:15])=[N:10][C:9]=3[C:4]([O:3][CH3:2])=[CH:5][CH:6]=2)[CH2:23][CH2:24]1)=[O:38]

Participants

7

Reactant 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 86588847Morpholine-4-carboxylic acid (4-methoxy-7-piperidin-4-yl-benzothiazol-2-yl)-amide hydrochloride

Product 1

HCID 865888504-{4-Methoxy-2-[(morpholine-4-carbonyl)-amino]-benzothiazol-7-yl}-piperidine-1-carboxylic acid methyl esterYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 0.05 g (0.12 mMol) morpholine-4-carboxylic acid (4-methoxy-7-piperidin-4-yl-benzothiazol-2-yl)-amide hydrochloride (1:1) in 3 ml THF were added 0.019 ml triethyl amine. At 0° C. 0.011 ml (0.13 mMol) chloro formic acid methyl ester was added dropwise and stirred for 1 h. Then a mixture of 5 ml sat. aqueous sodium bicarbonate and 10 ml water were added. This was extracted three times with 15 ml ethyl acetate, the combined organic phase were dried over sodium sulfate and evaporated to dryness in vacuo. One obtained 0.037 g (70%) 4-{4-methoxy-2-[(morpholine-4-carbonyl)-amino]-benzothiazol-7-yl}-piperidine-1-carboxylic acid methyl ester as a white solid. F.p.: 179-185° C.

Workup

  1. customAt 0° C
  2. additionwere added
  3. extractionThis was extracted three times with 15 ml ethyl acetate
  4. dry with materialthe combined organic phase were dried over sodium sulfate
  5. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-823bb1be5656447fa57e9dc288947681
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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