1,1-Dichloroethane → HCID 4088536, compound

HRID 1621271Notes

Reaction equation

HRID 1621271 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([S:10][CH2:11][C:12]([OH:14])=O)=[CH:2]1.[NH2:15][C:16]1[CH:20]=[C:19]([CH3:21])[O:18][N:17]=1.C1CN(C(Cl)=[N+]2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.ClC(Cl)C>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([S:10][CH2:11][C:12]([NH:15][C:16]2[CH:20]=[C:19]([CH3:21])[O:18][N:17]=2)=[O:14])=[CH:2]1

Participants

6

Reactant 5

HCID 63651,1-DichloroethaneHCID 661723-Amino-5-methylisoxazoleHCID 81531DiisopropylethylamineHCID 590707(1H-Indol-3-ylsulfanyl)-acetic acidHCID 27366521-(Chloro-1-pyrrolidinylmethylene)pyrrolidinium Hexafluorophosphate

Product 1

HCID 4088536HCID 4088536, compoundYield 71%

Procedure

2-((1H-indol-3-yl)thio)acetic acid (650 mg, 3.14 mmol) from Step B, 3-amino-5-methyl-isoxazole (616 mg, 6.28 mmol), PyClu (2.00 g, 6.28 mmol), and DIEA (1.36 mL, 7.85 mmol) were added to dichloroethane (25 mL) and microwave irradiated at 110° C. for 20 minutes. The solvent was removed in vacuo and the remaining residue purified on a silica gel column (0-70% ethyl acetate:hexanes over 33 min) to yield the desired product (642 mg, 2.23 mmol, 71% yield). LCMS>99% at 214 nm, RT=1.23 min, m/z=288 (M+1).

Workup

  1. customirradiated at 110° C. for 20 minutes
  2. customThe solvent was removed in vacuo
  3. customthe remaining residue purified on a silica gel column (0-70% ethyl acetate:hexanes over 33 min)

Sources & evidence

ORD record
ord-178121c4e56d4f31b1a6aa24e23d7dd0
Source dataset
uspto-grants-2014_07
Patent number
US08772509B2

Reaction notes

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