Dimethylamine → HCID 25174431, compound

HRID 549450Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.[NH2:13][C@H:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]#[N:24])[CH:21]=2)[CH2:16][C:15]1([CH3:26])[CH3:25].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.CNC>CN(C=O)C>[C:23]([C:20]1[CH:21]=[C:22]2[C:17]([CH2:16][C:15]([CH3:26])([CH3:25])[C@H:14]2[NH:13][C:10]([C:2]2[NH:1][C:9]3[C:4]([CH:3]=2)=[CH:5][CH:6]=[CH:7][CH:8]=3)=[O:12])=[CH:18][CH:19]=1)#[N:24]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 1H-indole-2-carboxylic acid (44.0 mg, 0.273 mmol), (R)-3-amino-2,2-dimethyl-2,3-dihydro-1H-indene-5-carbonitrile (34.0 mg, 0.182 mmol), BOP reagent (157 mg, 0.355 mmol), N-methylmorpholine (0.12 mL, 1.09 mmol) in DMF (0.5 mL) was stirred at 50° C. for 50 min. Dimethylamine (2.0 M in THF, 0.2 mL) was added to the mixture and the resulting mixture was stirred at 50° C. for 30 min. The desired title product (43.7 mg, 73% yield) was isolated as a white solid by prep. LCMS (M+H)+=330.33; HPLC. 1H NMR (500 MHz, DMSO-d6) δ: 11.6 (s, 1H), 8.53 (d, J=9.35 Hz, 1H), 7.70 (d, J=70 Hz, 1H), 7.60 (d, J=7.70 Hz, 1H), 7.62 (s, 1H) 7.46 (d, J=7.70 Hz, 1H), 7.44 (d, J=9.35 Hz, 1H), 7.29 (s, 1H), 7.18 (t, J=7.70 Hz, 1H), 7.03 (t, J=7.70 Hz, 1H), 5.38 (d, J=9.35 Hz, 1H), 2.86 (dd, J=22.5, 16.5 Hz, 2H), 1.21 (s, 3H), 0.94 (s, 3H). 13C NMR (125 MHz, DMSO-d6) δ: 161.1, 148.2, 144.1, 136.2, 131.4, 131.0, 127.9, 126.7, 125.7, 123.0, 121.2, 119.4, 118.8, 111.9, 108.8, 103.2, 61.0, 39.4, 39.2, 39.1, 38.9, 27.1, 22.2.

Workup

stirringthe resulting mixture was stirred at 50° C. for 30 min

Sources & evidence

ORD record: ord-fd210be306e94e179fd67136fe597735
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943658B2

Reaction notes

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