Diisopropylethylamine → HCID 86707705, compound

HRID 1408952Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](Cl)=[C:8]([C:11]([NH2:13])=[O:12])[CH:7]=[N:6][N:5]2[CH:14]=1.[NH2:15][C@@H:16]1[CH2:20][CH2:19][C@@:18]([CH3:22])([OH:21])[C:17]1([CH3:24])[CH3:23].CCN(C(C)C)C(C)C>CC#N>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([NH:15][C@@H:16]3[CH2:20][CH2:19][C@:18]([OH:21])([CH3:22])[C:17]3([CH3:24])[CH3:23])=[C:8]([C:11]([NH2:13])=[O:12])[CH:7]=[N:6][N:5]2[CH:14]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (Preparation 5, 38.3 mg, 0.140 mmol) and (1R,3R)-3-amino-1,2,2-trimethylcyclopentanol (from Step 2 of Intermediate 20, 20 mg, 0.140 mmol) in MeCN (1 mL) was added DIPEA (0.050 mL, 0.279 mmol). The reaction was sealed and heated to at 120° C. for 60 min. The reaction was cooled and concentrated then purified by flash chromatography on silica gel using 30-70% ethyl acetate/hexanes as the eluent to afford the title compound (47 mg, 86% yield). HPLC (Conditions L): retention time=7.21 min., (condition P): retention time=8.31 min.; LCMS: 382.97 (M+2); 1H NMR (CDCl3, 400 MHz) δ 10.51 (br d, J=9.4 Hz, 1H), 7.84 (s, 1H), 7.57 (d, J=1.7 Hz, 1H), 6.97 (d, J=1.8 Hz, 1H), 5.45 (br s, 2H), 4.69 (q, J=9.5 Hz, 1H), 2.38 (m, 1H), 1.99 (m, 1H), 1.79 (m, 1H), 1.56 (m, 1H), 1.27 (s, 3H), 1.01 (s, 3H), 0.98 (s, 3H).

Workup

customThe reaction was sealed
temperatureThe reaction was cooled
concentrationconcentrated
customthen purified by flash chromatography on silica gel using 30-70% ethyl acetate/hexanes as the eluent

Sources & evidence

ORD record: ord-8a7d53fb24ae45afa07abca86c527026
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921368B2

Reaction notes

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