N,N-Diethylethylenediamine → HCID 11656079, compound

HRID 1725947Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=2[C:13]=1[C:22]([OH:24])=[O:23])(=[O:10])=[O:9].ClC(Cl)(O[C:29](=[O:35])OC(Cl)(Cl)Cl)Cl.[CH2:37]([N:39]([CH2:43][CH3:44])[CH2:40][CH2:41][NH2:42])[CH3:38]>N1C=CC=CC=1>[CH2:37]([N:39]([CH2:43][CH3:44])[CH2:40][CH2:41][NH:42][C:29]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=2[C:13]=1[C:22]([OH:24])=[O:23])(=[O:10])=[O:9])=[O:35])[CH3:38]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of Example 294 (30.2 mg, 0.09 mmol), triphosgene (8.5 mg, 0.03 mmol), and pyridine (1 mL) was stirred for 3 hours at 70° C., treated with N,N-diethylethylenediamine (61 μL, 0.44 mmol), stirred for 18 hours at 70° C., concentrated, and purified by C18 reverse-phase HPLC using acetonitrile/water/0.1% TFA to provide the desired product (2.0 mg, 5%). MS (ESI(+)) m/e 489 (M+H)+; MS (ESI(−)) m/e 487 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 8.27 (s, 1H), 8.18 (d, 1H), 7.69 (dd, 1H), 7.53 (td, 1H), 7.47 (m, 1H), 7.10 (t, 1H), 6.95 (d, 1H), 6.65 (s, 1H), 3.19 (m, 6H), 2.66 (m, 4H), 1.66 (m, 4H), 1.20 (t, 6H).

Workup

concentrationconcentrated
custompurified by C18 reverse-phase

Sources & evidence

ORD record: ord-9e57f074ef5649aeb23e2f1d75682d4d
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491718B2

Reaction notes

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