HCID 21024364, compound → HCID 21024363, compound

HRID 1795602Notes

Reaction equation

HRID 1795602 reaction equation
C(N(C1C=CC2C(CC)=CCC(C)(C)C=2C=1)C1C=CC(C(O)=O)=CC=1)C.[CH2:27]([O:29][C:30](=[O:54])[C:31]1[CH:36]=[CH:35][C:34]([N:37](CC)[C:38]2[CH:47]=[CH:46][C:45]3[C:44]([CH2:48][CH3:49])=[CH:43][CH2:42][C:41]([CH3:51])([CH3:50])[C:40]=3[CH:39]=2)=[CH:33][CH:32]=1)[CH3:28]>>[CH2:27]([O:29][C:30](=[O:54])[C:31]1[CH:32]=[CH:33][C:34]([NH:37][C:38]2[CH:47]=[CH:46][C:45]3[C:44]([CH2:48][CH3:49])=[CH:43][CH2:42][C:41]([CH3:50])([CH3:51])[C:40]=3[CH:39]=2)=[CH:35][CH:36]=1)[CH3:28]

Participants

3

Reactant 2

HCID 21024364HCID 21024364, compound2×HCID 22218306HCID 22218306, compound2×

Product 1

HCID 21024363HCID 21024363, compound

Procedure

PNMR (300 MHz, CDCl3) δ 1.18 (t, 3 H, J=7.3 Hz), 1.23 (s, 6 H), 1.39 (t, 3 H, J=7.1 Hz), 2.17 (d, 2 H, J=4.0 Hz), 2.46 (d, 2 H, J=7.3 Hz), 4.34 (q, 2 H J=7.1 Hz), 5.70 (t, 1 H, J=4.0 Hz), 6.07 (s 1 H, NH), 7.00-7.03 (overlapping d & dd, 3 H), 7.11 (s, 1 H), 7.25 (d, 1 H, J=8.6 Hz), 7.93 (d, 2 H, J=8.6 Hz). 4-[Ethyl-(5-ethyl-8,8-dimethyl-7,8-dihydro-naphthalen-2-yl)-amino]-benzoic acid ethyl ester (Compound 74). Following General Procedure D, 4-(5-Ethyl-8,8-dimethyl-7,8-dihydro-naphthalen-2-ylamino)-benzoic acid ethyl ester (Compound 73), (0.13 g, 0.38 mmol) was reacted to give the title compound as a solid. PNMR (CDCl3): δ 1.19 (t, J=7.4 Hz, 3 H), 1.22 (s, 6 H), 1.26 (t, J=7.1 Hz, 3 H), 1.36 (t, J=7.1 Hz, 3 H), 2.21 (d, J=4.5 Hz, 2 H), 2.42 (q, J=7.3 Hz, 2 H), 2.489 (q, J=7.4 Hz, 2 H), 3 80 (q, J=7.1 Hz, 2 H), 4.316 (q, J=7.1 Hz, 2 H), 5.76 (t, J=4.5 Hz, 1 H), 6.71 (d, J=8.9 Hz, 2 H), 6.99 (dd, J=2.2, 8.2 Hz, 1 H), 7.12 (d, J=2.23 Hz, 1 H), 7.30 (d, J=8.2 Hz, 1 H), 7.84 (d, J=8.9 Hz, 2 H). 4-[Ethyl-(5-ethyl-8,8-dimethyl-7,8-dihydro-naphthalen-2-yl)-amino]-benzoic acid (Compound 75). Following General Procedure E, 4-[Ethyl-(5-ethyl-8,8-dimethyl-7,8-dihydro-naphthalen-2-yl)-amino]-benzoic acid ethyl ester (Compound 74), (88 mg, 0.23 mmol) was reacted to give the title compound as a solid. PNMR (δ6 acetone) δ 1.18 (t, J=7.3 Hz, 3 H), 1.24 (s, 6 H), 1.25 (t, J=7.1 Hz, 3 H), 2.22 (d, J=4.5 Hz, 2 H), 2.53 (q, J=7.3 Hz, 2 H), 3.87 (q, J=7.1 Hz, 2 H), 5.80 (t, J=4.5 Hz, 1 H), 6.79 (d, J=9.2 Hz, 2 H), 7.08 (dd, J=2.2, 8.1 Hz, 1 H), 7.23 (d, J=2.2 Hz, 1 H), 6-Bromo-1-isopropyl-4,4-dimethyl- 1,2,3,4-tetrahydro-naphthalen-1-ol (Compound 76)

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-5073b3ee8fc447dcb669624361937dbc
Source dataset
uspto-grants-2006_04
Patent number
US07026487B2

Reaction notes

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