Diisopropylethylamine → HCID 59232897, compound

HRID 2426983Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[CH:17][CH:16]=2)[C:9]([CH3:14])([CH3:13])[C:10](O)=[O:11])=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.CC1C2C(=CC=CC=2)C([C:50]2[N:51]=[C:52]([NH2:55])[S:53][CH:54]=2)=CC=1.C(N(C(C)C)CC)(C)C>CC#N>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)=[CH:17][CH:16]=2)[C:9]([CH3:14])([CH3:13])[C:10]([NH:55][C:52]2[S:53][CH:54]=[CH:50][N:51]=2)=[O:11])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of the acid of Preparation 14a (51 mg, 0.142 mmol) in CH3CN (3 mL) were added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC) (48.3 mg, 0.213 mmol) and 1-hydroxy-7-benzotriazole (HOBt) (34 mg, 0.213 mmol). After stirring for 5 minutes, to the solution were added 4-(4-methyl-naphthalen-1-yl)-thiazol-2-ylamine (50.4 mg, 0.426 mmol) and diisopropylethyl amine (0.742 ml, 0.426 mmol). The reaction was heated at 75° C. for 12 hours. The reaction mixture was filtered, and purified by preparative HPLC to give the title compound of Example 222 as a white solid (36 mg, 58% yield). LC/MS (m/z) 440.17 [(M+H)+]; HPLC Rt: 3.12 min. 1H NMR (400 MHz, CDCl3): δ 7.34 (1H, m), 7.18-7.26 (5H, m), 6.79-6.93 (4H, m), 4.42 (1H, s), 3.78 (4H, m), 3.06 (4H, m), 1.34 (6H, s). LC/MS (m/z) 440.17 [(M+H)+]; HPLC Rt: 3.120 min.

Workup

filtrationThe reaction mixture was filtered
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-3f3ab3ba2a2a4b939ebfb89e6544bba9
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968577B2

Reaction notes

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