1,4-Dioxa-8-azaspiro(4.5)decane → HCID 11993591, compound

HRID 1364498Notes

Reaction equation

HRID 1364498 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[S:15][C:14]([S:16](Cl)(=[O:18])=[O:17])=[CH:13][CH:12]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].[O:20]1[C:24]2([CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[O:23][CH2:22][CH2:21]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[O:20]1[C:24]2([CH2:29][CH2:28][N:27]([S:16]([C:14]3[S:15][C:11]([C:7]4[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][C:8]=4[CH3:10])=[CH:12][CH:13]=3)(=[O:18])=[O:17])[CH2:26][CH2:25]2)[O:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 81531DiisopropylethylamineHCID 866225625-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride

Product 1

HCID 11993591HCID 11993591, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-[2-(acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride, prepared as in Step 1 of example 9 (200 mg; 0.59 mmol; 1 eq.), is dissolved in DCM (10 ml). 1,4-Dioxa-8-azaspiro[4.5]decane (170.0 mg; 1.19 mmol; 2 eq.) and DIEA (460.4 mg; 3.56 mmol; 6 eq.) are added. After one hour, the solvents are evaporated. The crude product is purified by preparative HPLC, affording Compound (18) as yellow solid (96 mg; 37%). 1H NMR (DMSO-d6) δ 1.66-1.78 (m, 4H), 2.15 (s, 3H), 2.45 (s, 3H), 3-3.15 (m, 4H), 3.83 (s, 4H), 7.31 (d, J=3.8 Hz, 1H), 7.61 (d, J=3.8 Hz, 1H), 12.15 (br s, 1H). M−(ESI): 444.25; M+(ESI): 442.23. HPLC, Rt: 3.39 min (purity: 99.6%).

Workup

  1. customthe solvents are evaporated
  2. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-d4b2753e703b4006b8ddc5205833574e
Source dataset
uspto-grants-2011_02
Patent number
US07888379B2

Reaction notes

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