Dichloromethane → HCID 66661918, compound

HRID 969235Notes

Reaction equation

HRID 969235 reaction equation
Cl.Cl.[N:3]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3([C:16](Cl)=[O:17])[CH2:15][CH2:14]3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4]1.CC1(C)C2CCC1(CS(O)(=O)=O)C(=O)C2.[NH:34]1[CH2:38][CH2:37][C@@:36]2([C:46]3[CH:45]=[CH:44][N:43]=[CH:42][C:41]=3[C:40](=[O:47])[O:39]2)[CH2:35]1.C(Cl)Cl.C(N(CC)C(C)C)(C)C>C(OCC)(=O)C>[N:3]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3([C:16]([N:34]4[CH2:38][CH2:37][C@@:36]5([C:46]6[CH:45]=[CH:44][N:43]=[CH:42][C:41]=6[C:40](=[O:47])[O:39]5)[CH2:35]4)=[O:17])[CH2:15][CH2:14]3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 86602288HCID 86602288, compoundHCID 86602290HCID 86602290, compound

Product 1

HCID 66661918HCID 66661918, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(6-azetidin-1-ylpyridin-3-yl)cyclopropanecarbonyl chloride dihydrochloride (64.00 mg, 0.0002067 mol) and (7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonic acid-(1R)-3H-spiro[furo[3,4-c]pyridine-1,3′-pyrrolidin]-3-one (1:1) (87.3 mg, 0.000207 mol) in methylene chloride (1.00 mL, 0.0156 mol) was added N,N-diisopropylethylamine (0.144 mL, 0.000827 mol) at 0° C. The reaction mixture was stirred at rt for 1-2 h. Upon completion the reaction mixture was diluted with ethyl acetate and washed with water and brine successively, dried with sodium sulfate, filtered, and concentrated. The crude product was purified by prep-LCMS twice to obtain the product as a TFA salt. LCMS: m/z 391.2 (M+H)+.

Workup

  1. washwashed with water and brine successively
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by prep-LCMS twice

Sources & evidence

ORD record
ord-79195c2371934ef7bb2f04d962cdbe60
Source dataset
uspto-grants-2007_12
Patent number
US07304081B2

Reaction notes

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