1,2-Dichloroethane → HCID 86671985, compound

HRID 874290Notes

Reaction equation

HRID 874290 reaction equation
[CH3:1][N:2]1[CH2:5][C:4]2([CH2:14][C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[C:10](/[CH:16]=[CH:17]/[C:18](O)=[O:19])[CH:11]=3)[O:6]2)[CH2:3]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH2:35][O:36][CH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][O:38]1>C(Cl)Cl>[CH3:1][N:2]1[CH2:3][C:4]2([CH2:14][C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[C:10](/[CH:16]=[CH:17]/[C:18]([NH:35][O:36][CH:37]4[CH2:42][CH2:41][CH2:40][CH2:39][O:38]4)=[O:19])[CH:11]=3)[O:6]2)[CH2:5]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 67071672HCID 67071672, compound

Product 1

HCID 86671985HCID 86671985, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of (E)-3-[1′-methyl-4-oxo-spiro(chromane-2,3′-azetidine)-6-yl]-acrylic acid (400 mg, 1.29 mmol) in DCM (16 ml) was treated with TEA (0.30 ml, 2.2 mmol) and then with EDC (420 mg, 2.20 mmol), HOBt (297 mg, 2.20 mmol) and NH2OTHP (204 mg, 1.75 mmol) following the procedure described in Example 30, Step B, giving (E)-3-[1′-methyl-4-oxo-spiro(chromane-2,3′-azetidine)-6-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide (340 mg) as a light yellow solid.

Sources & evidence

ORD record
ord-ae603f55c1a74570a038e438ae2b67a4
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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