Azetidine → HCID 178508625, compound

HRID 1163202Notes

Reaction equation

HRID 1163202 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([C@@H:12]3[CH2:15][C@H:14]([CH2:16]OS(C4C=CC(C)=CC=4)(=O)=O)[CH2:13]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[NH:28]1[CH2:31][CH2:30][CH2:29]1>CN(C=O)C>[N:28]1([CH2:16][C@@H:14]2[CH2:13][C@H:12]([N:8]3[C:4]4[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=4[C:10]([I:11])=[CH:9]3)[CH2:15]2)[CH2:31][CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 10422AzetidineHCID 178427770HCID 178427770, compound

Product 1

HCID 178508625HCID 178508625, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The DMF (3 mL) solution of cis-toluene-4-sulfonic acid 3-(4-amino-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)-cyclobutylmethyl ester (see above for its preparation) (63 mg, 80% purity, 0.10 mmol) and azetidine (12 mg, 2 eq.) was stirred at 50° C. overnight in a sealed tube. The reaction mixture was used directly for further reaction. MS (ES+): 384.1 [MH+]. HPLC: tR=1.4 min (polar—5 min). For 1H NMR analysis, a small sample was taken out for HPLC purification. 1H NMR (DMSO-d6, 400 MHz): δ=1.99-2.06 (quintet, 2H, J=6.9 Hz), 2.08-2.22 (m, 3H), 2.49-2.53 (m, 2H), 2.54-2.56 (d, 2H, J=6.4 Hz), 3.15-3.19 (d, 4H, J=7.2 Hz), 5.01-5.10 (quintet, 2H, J=8.7 Hz), 6.69 (brs, 2H), 7.80 (s, 1H), 8.16 (s, 1H).

Workup

  1. customThe reaction mixture was used directly for further reaction
  2. customHPLC: tR=1.4 min (polar—5 min)
  3. customFor 1H NMR analysis, a small sample was taken out for HPLC purification

Sources & evidence

ORD record
ord-24f8b28c201e41e4a0c911f04a91bf1b
Source dataset
uspto-grants-2010_10
Patent number
US07820662B2

Reaction notes

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